RICK (00:00.92)
Hello Tyler.

Tyler King (00:01.314)
Happy New Year!

RICK (00:03.956)
It's still December, technically, but I think we'll publish this on a on the first.

Tyler King (00:07.042)
I think I'll get this out today, which is New Year's Eve, so...

RICK (00:12.046)
Okay. Well, happy new year in advance. You doing anything fun?

Tyler King (00:15.938)
Yeah, man, life really changes when you have a kid. We've got one of Shelly, my wife's best friends from college, is in town with her toddler and then the friend from out of town, some of her good friends that used to live in San Francisco with her now live in St. Louis. So anyway, three families with kids all getting together and I think we're celebrating the ball drop at 7 p.m. So very different from all my previous New Year's.

RICK (00:41.87)
Oof.

How do you make the ball drop at 7 p.m.? Do you watch last year's?

Tyler King (00:48.352)
I think there's a few options. One is to watch like the, it's not technically a ball drop, I guess, but like watch the London New Year's Eve. That's six hours from here. So like there's actually a British themed brewery nearby here. We're not going to it, but they do a family friendly New Year's party where they have the live stream from London, which is perfect because it's a British pub. Anyway, that's one way to do it.

RICK (01:14.072)
That is terrific. We've been the last few years watching the New York ball in Utah, which is a 10 PM drop. So that's not bad.

Tyler King (01:21.921)
Yeah.

Yeah. Do the kids stay up for that?

RICK (01:26.67)
No, they have, they're in bed by 738 every night.

Tyler King (01:28.098)
Rick just made this face at me like, are you an idiot?

RICK (01:32.399)
No, we there are different parenting tactics out there. Like some parents are like, Hey, no, we're not we're not we're gonna have our kids with us. We're not gonna worry about like sort of sleep schedules. But a lot of the literature said there's a counter counter approach, which is sleep is important for, you know, little very small kids and having them on a schedule and keep them on a schedule is important. We fall more in that camp. But no judgment. If you're if you're the opposite.

Tyler King (01:51.266)
Mm-hmm.

Tyler King (01:58.038)
I fall more in that camp, I do, like having, I don't know if it even works this way, but our hope is to like occasionally disrupt it so the kids are capable of surviving without, like sometimes disruptions unavoidable. For example, we just traveled to the West Coast and like the kid got off the plane at midnight hour time. And it's just like, there's nothing you can do about that one, you know?

RICK (02:20.686)
Oh, of course not. Yeah, that's just like, when it's it's necessary, it happens. But day to day, you know, the priority is getting them on a on a sleep schedule for us. And they don't care about the ball drop. All they want to do is watch, you know, they want to watch Zootopia to you know, what am I doing for years? I haven't even thought about it, honestly. I'm working today. So I've got a pretty busy day and then we'll hang out here and

Tyler King (02:29.686)
Yeah. Cool. What are you doing for New Year's? of course.

Tyler King (02:37.195)
You

RICK (02:49.196)
We've done some big stuff for Christmas and Thanksgiving this year. So I think it'll be low key. I'm excited about this episode, man. Like I, this time last year I was going through a lot. and I, I I went and listened to the, to the, the annual episode last year, which I hadn't, I didn't have time to do last year. and it was really good for me to listen to that and go, wow, okay. I had no, I had no prep coming into this episode last year.

Tyler King (02:57.12)
Yeah.

Tyler King (03:15.202)
you

Mhm.

RICK (03:18.176)
I had no idea what was going to happen or what I was signing up for. I was so oblivious and a year happened.

Tyler King (03:25.9)
That's interesting. should have done that. didn't. read reviewed the notes that from the show notes last year, but I didn't listen to it. what's your before we get into kind of the full review here. What's your take on last year's episode? Like, because that probably you're more prepped this time. I'm not. I'm the same amount of prepped. Like whatever we got wrong or whatever last year is probably just going to repeat this year.

RICK (03:48.463)
I mean, the fundamental thing I was not prepared for what I signed up for. So I mean, it's hard without giving context, but like I had a massive life event, which we'll talk about as part of my reflection from last year. And none of my goals were related to that.

Tyler King (04:05.078)
Well, you didn't know it was gonna happen though. Or did you? You did one year ago.

RICK (04:07.958)
I did. We Yeah, it happened in December. So our so I might my take on the episode is like I was living in La La Land.

Tyler King (04:11.925)
okay.

RICK (04:18.542)
Yeah. And it was part of, cause I didn't prep. Um, now the difference this year is I spent a lot of time reflecting and it was, I had to process a lot of emotions that, um, you know, when you, when you don't reflect, it's like, you could just pretend about, you know, things didn't happen or you don't feel certain things, you know, or, uh, you didn't make mistakes. Um, and, uh, this year I reflected very deeply and it was, it was a lot to process.

Tyler King (04:44.162)
All right, well, I hope in a productive way.

RICK (04:47.86)
very, very productive. I'm like, you know, when you go through reflection and planning, like there's the reflection part that can be really painful. But once you get through it, and you turn it into a plan, you're like, my god, I feel so much better. That's where I'm feeling right now.

Tyler King (04:58.914)
Yeah, yeah. All right, well do you wanna dive in? Sounds like you've got some stuff if you wanna start.

RICK (05:04.91)
Yeah, yeah. So, I mean, I think the way we typically do this is we'll do personal reflection and goals back and forth. And then we'll do we'll kind of reflect on that and then go to professional goals. Is that the format you're thinking this year? Cool. Well, so so I'll just start with summarizing like the themes of the year. And I'm going to do this, you know, both for this year.

Tyler King (05:18.838)
Yeah. Yeah.

RICK (05:31.841)
or last year, what were the themes of what I would like the themes to be this year intentionally last year was like the three words that I used to describe it as like reactive or reacting, survival, and then postponing, like I felt and I'll get into like why I felt those things but like it was basically my one of my least proactive like forward moving years professionally, and personally, in a long long time. And I'm sure that like

As I look backwards, moving forward, I'm going to go, man, this was a year of growth, but like right now it just feels like what happened. I got punched in the face in the episode last year. You talked a lot about the Mike Tyson quote. everyone has a plan to get until they get punched in the face. I got, I got punched in the face last year. but the main, the main sort of, thing I'm not even going to try to hit on our, goals that I set because they were stupid. yeah. Like the, the

Tyler King (06:07.126)
Hmm.

Tyler King (06:11.735)
Yeah.

Tyler King (06:22.47)
They're just wrong. You didn't get back time for things like skiing and basketball?

RICK (06:28.306)
No. I don't know what I was thinking. I saw I'm kind of embarrassed. In one way, I'm like super embarrassed that I set those goals. But at the same time, I was just like not thinking clearly.

Tyler King (06:32.737)
you

Tyler King (06:39.158)
Yeah. If anyone's curious, I will post last year's goals in the show notes just so you can review what they were. But yeah, you'll skip those and yeah.

RICK (06:43.488)
No. Yeah. Yeah, I was like, take one personal day every one to two months. No, I did not do that. Get time back for things I love. No, I did not do that. I did. mean, I started writing again. I skied a good bit a little bit, not a lot. And I did do basketball stuff. But that wasn't like a significant progression. Then another was to have a family. We did. So I that that but I get it was like was

Tyler King (07:02.742)
Yeah, you did take family vacations.

RICK (07:09.186)
Why did I put pressure on myself to have family vacations? I don't even know. I shouldn't have been worried about any of these three things. should have. So let me just kind of jump to like the, the, the, the core point here is last December we dealt with a family crisis. We over, we unexpectedly took over parenting our niece who was 15 at the time. and it was now 16 and our nephew who was 21 at the time and who is now 22. We had to take over their, their dad's finances, get them settled. they, they, they live with us now.

we had to take, it was, was a massive way to deal with, court systems for guardianship. had to, help them, you know, watch, their, their dad go through some serious stuff, help them process it. and it is a year later and it's filled. feels like we just started. and so, it was super hard. It became the number one priority for the year. and I think if I could go back and do it again, I would have been more like.

wreck real like realistic about what this meant. And I think as a result, I would have set proper expectations for myself. I think a lot of things would have gone smoother this year. And anyway, I'm very proud of Sable and I for doing what we did. And I feel I'm also proud of these two kids like they're they're excelling as best I mean, better than

most people despite the circumstances that they're going through. And I want to spend I've intentionally chose the words that I shared to share this because it's a private matter. But I can't talk about my my year without explaining that this happened and it was all encompassing and continues to be.

Tyler King (08:42.082)
Mm-hmm.

Tyler King (08:56.448)
Yeah. Yeah, I admire the hell out of you guys for also, yeah, I mean, dropping everything and making that happen. I get what you're saying about a year ago, should have, you should have realized that that was going to be the only thing, but whatever the case, I mean, this reminds me of like a much lower stakes version of this. I used to listen to a podcast called Money for Couples. It's just a personal finance podcast.

And he's all about, here's how you get your financial shit together. And then he interviews couples in each episode. But sometimes the couple's like, we just had a baby. And he's just like, oh, well forget about finances for a year. This isn't the time for that, right? I don't know if you are beating yourself up about not getting anything else done, but certainly you shouldn't, right?

RICK (09:47.631)
That's exactly right. And I'm actually not I'm actually more being myself up for trying to prioritize the wrong things. And the impact that that maybe I didn't have as a result on other people and family. And I certainly did don't get me wrong, but it wasn't as intentional as I would have liked to be. Yeah, exactly. Yeah. I mean, if what why? Why was I reactive survival postpone? Well, it's like,

Tyler King (09:55.307)
Mmm, okay.

Tyler King (10:07.724)
That's the reactive thing you're talking about. Gotcha. Okay.

RICK (10:17.77)
I tried to do things I shouldn't have been trying to do. I wasn't focused on the right things. And as a result, I kept getting like surprised by what, what was needed of me. And that was, that was not the right thing. That was my mistake, not anyone else's. So, I'll go through, a couple more reflections on like, cause, cause it was heavily dominated. My, year was heavily dominated by personal and family. So health wise and personal wise, I'm my

Tyler King (10:28.706)
Mm-hmm.

RICK (10:46.54)
I made a lot of progress. decided to prioritize weight in the mid year. I'm down 20 pounds, as light as I've been since I can remember, like park city days. And, you know, I'm, I'm consistently reading fiction again, which has been a really fun thing to do as a bedtime routine. I've read a lot of really good books. I've also started writing daily every morning I'm writing, which is, it's not, you know, I'm not publishing it, but, but it feels good just to have that.

reflective process built into my daily routine. Um, what's, what's missing is, um, I'm doing far less nonfiction reading than I used to. Like I'm still reading a lot of articles, particularly around in the AI space. And I'm interacting with chat GBT, which you could argue is a form of nonfiction reading. Um, but I'm not publishing like nonfiction, right? I'm not reading nonfiction and I'm not publishing notes and like my learnings, like I want to, uh, it's a big, it's an important part of.

of just like my self-improvement process. And I do feel like if I had been doing that more proactively this past year, I would have caught the things that it took me a full year to caught earlier because I, I lost some of this like important spiritual routine that I have. I don't, I don't, I'm not a church goer, you know, I rely on my, my reflective writing and self-improvement to kind of drive home those moments. And I missed on that. and then I, I, I feel like,

this AI, I'll spend a lot of time talking professionally and personally about like this AI trend. and, I definitely feel like I still lack the depth of knowledge, technically, to graphs, to take advantage of the full advantage of the AI, technological shift. And, that's something I'm going to try, probably try to address this year when we get to our goals. any, any questions or thoughts on, on that?

Tyler King (12:35.532)
Questions on the AI point, but you said we're gonna talk more. Should I save them for later? Okay.

RICK (12:37.75)
Yeah. Yeah. Save that for later. I'll, I'll jump to family real quick and then I'll, from, know, reflecting what, one, one thing that I spent a lot more time focused on the family this year than I have in the years past. and as I was going through my reflection, because I spent more time, there were so many things to be like thankful for and proud of moments that mattered, if you will. Avery is our daughter and she's

She's chattering now and talking and it's like a whole nother world. Oliver started doing soccer lessons. He learned how to swim without a life vest. He's skiing. did. He learned how to ride his bike. Like there was these big events that were, I was very present for and was awesome. one thing that I didn't, I didn't anticipate was I was at one of the routines I had with my niece, my niece, who's in high, who's in high school is before she got her license, I would drive her to school every morning. which you kind of

It's that gets like, that's a big chain life change is your morning routine changing. But anyway, that was like super, the, the, drive to school is such a, intimate, moment, with people, with, especially when it's one-on-one, the, silence and then you ended up talking. and if you do that consistently over weeks and weeks and weeks and days and days and days, it, you develop a deeper relationship. And that was, that was like something that I

Tyler King (13:39.98)
Yeah.

RICK (14:05.582)
She's, she's 16 now and she drives herself to work, to school. And I miss those mornings with her. Um, which has been interesting.

Tyler King (14:11.574)
Yeah. That's like making boring, long lasting, regular interactions with someone is the only way to form strong relationships, I think. I think this is one reason. I have some of these people I know have so many of these where you feel like you're being social. You're going out, you're catching up with this person, you're getting coffee with that person. But that you have to sit in a car quietly or something like it.

I totally get what you're saying. I think this is also why, sorry, I'm totally changing topics here. Like working in person with people is so important because when you're remote, you're like, I'm only talking to them when we have a meeting scheduled and there's an agenda and you try to get off it as quickly as possible so you can get back to work. But that like, we're just sitting here having lunch and we're not even having lunch together. We're just having lunch next to each other. Like that type of thing is the only way to form a real relationship.

RICK (15:06.894)
I I agree. I got to figure out how to replace that. it's, one, one area that, that we, we, we also did is I would take her skiing one, one day out of the weekend and she fell in love with skiing and is all that's like what she wants to do every day now. yeah. Yep. our new, our, another area is like previous years, I would complain about the house that we bought and how hard it was to, to go through that process. it's

Tyler King (15:12.13)
Yeah.

Tyler King (15:22.698)
I mean, if you live in Utah, you just have to.

RICK (15:35.596)
We've it's settled. We're good. It's great. We're very grateful for it and it works. I'm home for dinner. Good.

Tyler King (15:37.026)
That's great.

Tyler King (15:41.788)
Is it, you think of this as your forever home?

RICK (15:45.615)
No, I don't. The major thing that I mean, it it could be. So I would say yes, it could be but but it lacks a couple of location is the problem. It's not the house itself. It's just a far too far away from things that we like to do. We don't have time to do those things right now. So it doesn't matter. But yeah, but at some point in the future, we will want to do those things.

Tyler King (16:01.09)
Gotcha.

Tyler King (16:08.479)
So who cares?

RICK (16:13.93)
I'm, home for dinner most days, like with the family and I I'm actually cooking dinner. I never thought I would be a chef, but I cook, I prepare dinner at least two out of seven days a week. I'm not talking about like ordering door dash. I ordered door dash, maybe two of the other seven, five days a week, but, the days I'm cooking, I'm cooking steaks, salmon, you know, ribs on my smoker or on my grill. And it's, people.

Tyler King (16:31.33)
Mm-hmm.

RICK (16:41.388)
I've gotten not great at it, but good at it and people seem to enjoy the food and I didn't think I would enjoy that. I would have thought I have would hate it honestly. And I it's been a great source of fulfillment.

Tyler King (16:50.23)
Yeah. Can you articulate what you enjoy? Because I, with the daughter now, my wife and I, neither of us cooked before and we're both like, that is a thing we're going to have to do. We can't get takeout every single night with a kid. What do you enjoy about it?

RICK (17:08.142)
when everyone comes to the table together after you've set the table and they are, they haven't thought about food at all. Right. and they're coming from whatever they were doing and they're coming together and they go, this is so good. And everyone's happy. I don't know. I, it's just this like, it's setting up an experience, with a family comes together.

Tyler King (17:34.888)
I get that. Yeah, that that resonates with me more than other answers I've heard. I've asked this to a number of people and most people are like the cooking itself is what they enjoy, which I just don't think I'm ever going to relate to. But yeah, the because I'm like this with cocktails. It's obviously more trivial of a thing. You don't not gain sustenance from drinking cocktails. But when you have people over and there's.

RICK (17:44.559)
no.

Tyler King (17:59.06)
eight people sitting at the table and you bring out their drinks and everyone drinks something they've never had and it kind of delights them. Yeah, okay, I get that.

RICK (18:05.12)
Yeah, that's that. Yeah. And I would say if that didn't happen, I would not like cooking. I don't enjoy the process of cooking.

Tyler King (18:11.776)
So if you sucked at it, you would not enjoy it.

RICK (18:13.678)
Oh yeah, definitely. And I did suck at it for awhile. Like that's how it started. It's nothing worse than pulling out, know, burnt shrimp and trying to get people to eat it and just apologizing profusely. uh, the, the vacation highlight of the year, cause we did do a lot of family vacations was going to Charleston for a week. We rented a beach house at a pool. Oliver just like fell in love with swimming and that's where he learned how to swim. And it was just awesome. Um, I want it, we're going to go back. So

Tyler King (18:17.223)
Mm-hmm.

Tyler King (18:25.324)
Yeah.

RICK (18:42.422)
I hope I hope I shouldn't say we are going to I hope we go back because that was a really, really fun experience. Anyway, that's my sort of like reflection. I have never reflected this personally before. Like my, my year was very rich and hard in some ways, but very rich from a personal and family perspective.

Tyler King (18:45.674)
Mm-hmm. Cool.

RICK (19:03.006)
I'll shift to 2026 goals. and, apologize for dominating the first hour of this episode, but, Yep. Yep. So the, the annual semi annual themes. So I, what I, I want to be intentional about how I feel at the end of this year, if I can. and the, the three themes that I'm picking to like constrain where I'm focusing in.

Tyler King (19:11.788)
That's the format we've chosen.

RICK (19:31.118)
2026 personally is the first is getting back to basics. I've lost a lot of like the basics things out of reactiveness. And part of my reflection process, I was getting mad about it. You know, I was like, Oh, I'm so mad that, you know, this was done to me. And it's like, No, no, I actually lost discipline. I Yeah, yeah.

Tyler King (19:54.07)
Well, a little of both, though. Like, you can be... If I can critique you for a second, I think a thing you struggle with is you think you're more... like, you have more agency than any real person does. Like... which is a great quality to have in terms of being effective, right? To believe you're helpless is not a productive feeling, but it is true sometimes, and in this case, you were kind of helpless.

RICK (20:06.52)
Yeah.

RICK (20:14.382)
Yeah. So thank you for saying that I spent through my reflection. spent a lot of time reading and writing about agency. and I think I, there was a point in time, this is going back to like kind of the, took too long to reflect and, and, and get, get where I got in the last week. and I did have agency for that and I I lacked it. and, I, and so, yeah, there was a point at which I needed to

Tyler King (20:32.578)
Mm-hmm.

RICK (20:43.574)
make changes this year and I didn't, I didn't make them until now. And I, I regret that. So thank you for calling that out though. I appreciate you saying that. so getting back to basics, going from reactive to proactive or from surviving to thriving, shifting from a strategy of playing, this is a big one. Okay. I just want to, this, this is, I I'm happy to spend time explaining this and like philosophically, like shifting from a strategy of playing it safe and reducing risk to taking smart risk and being okay.

looking a little foolish. I, I have played it very safe since I've had kids personally and professionally. I have not taken a lot of risks. I have, I have been very, very safe. I've, I've, I've actively reduced risk and I'm ready to start, shifting that strategy to, you know, both like doing things that might make me look bad, or might result in failure and

taking more taking risk, but, making sure that it's like either asymmetric in my favor or I won't regret it, but being intentional about taking risk.

Tyler King (21:54.122)
Yeah, I like this one a lot and I want to think about this for myself as well because as you're, you know how sometimes someone else is talking about themselves and you hear it you're like, that's me. I also think I've not taken much risk and let me ramble for a second here. I sometimes question like, why am I a somewhat successful entrepreneur? I mean, listen, I'm talented, but like in the way that

If you grow up privileged, surrounded by people who are educated and talented, everyone I know is talented. I don't know anyone who's not in the top 10 % of everything they do. Just because average is very mediocre. Being in the top 10 % is not great. Being in the top 1 % is not even really great. Being in the top 0.1 % is great. I'm not in the top 0.1 % of anything. I'm in the top 10 % of a lot of stuff. That's not enough to be successful in entrepreneurship.

If I reflect on like what one quality, if I had to pick one, got me here, it's risk, understanding risk well. And there are two specific moments. One, when I got my job offer to work at Zane Benefits with you in Utah, I dropped out of college. did technically, I negotiated with the university. They still gave me my degree, but I, at the time I thought I was dropping out, moved to Utah. Everyone thought I was crazy. I probably was, but I was like,

If this doesn't go, this is a hot startup. I've never had an opportunity like this before. If this doesn't go well, I can just go back to school. It wasn't a risk is the thing. Everyone thought it was hugely risky. And I realized there's no risk here at all. And then the second one was two years into that quitting and going to start my own business. And again, everyone thought and moving to San Francisco and everyone thought I was crazy. And again, I was like, you think I can't get another job if this fails? Like I'm highly employable. This will be fine. Even if this whole thing fails, there's zero risk.

RICK (23:49.826)
I'll be even more playable after this.

Tyler King (23:51.554)
Yeah, exactly. and I think you're in the, I like that you're saying it will be embarrassing because the reality is there is no actual risk to you aside from embarrassment, right? Like there's no financial risk. You're both in the same way I was, you're highly employable and you have, I imagine a pretty stable financial situation. You're, you're married to someone who has a really good job. Like the only risk is that you get egg on your face.

RICK (24:19.608)
So thank you. think you totally get what I'm saying here. And I agree with everything you said. If I reflect on any of my long-term moderate success, it goes back to taking calculated risks. And I have not done that in a while.

Tyler King (24:34.562)
So can I, know we're already gonna have a long episode, can I go a little deeper on this and ask you a question, which is why? If I wanted to get defensive about myself, why am I not taking as many risks now? I might say, I already have what I want. That's probably a cop out. I probably should be taking risks and that's just a coward's way of explaining why I'm not. But I'm curious for you, what do you hope to get out of these risks?

RICK (24:38.605)
Yes.

RICK (25:03.458)
That's a very good question. Some of this stuff is private and so can't, I don't want to go too specific here, I'll try to explain it as.

I mean, fundamentally it's living a, living a life of meaning. and when I think about my, my most cherished moments, or like when I look back, it's not, when I look back and go, man, this was, that was the best. It's when I'm like fighting, for something that I believe in, and building, that state of, so it's, I guess it is towards what I want, which is like, building something, being

having more agency and control, independence, sort of thing. in a lot of ways, yeah, I guess you could say there's areas that I don't have, but I want, and I want to go get those things.

Tyler King (26:01.826)
So I heard two things. One is the destination and one is the journey. We're all talking about AI a lot these days, of course, and one of the possible things that could happen is we don't have, we aren't needed anymore, which gets you to the destination, gets us all to the destination we want, but it ends, well, okay, because the journey is the destination, right?

RICK (26:23.106)
That's not the destination I want.

Correct.

Tyler King (26:28.886)
the act of struggling, the act of being challenged and learning and growing in many cases is more important than where it actually gets you. So what I'm hearing from you, maybe there are some more concrete destinations, like some actual goals, but you need to take risk because taking risk in and of itself is the point of life, kind of.

RICK (26:46.498)
Exactly. That's what living is. Yeah. all right. So, I'll, let me just kind of wrap up my personal goals for the year I'll hand it to you. I'd love to hear your personal reflection. so I just want to get back to basics, in my personal life for me, what this looks like, is like, this is personal health, I would say it's, continue my weight loss journey.

Tyler King (26:48.192)
Okay, I'm going to think about that some more.

RICK (27:13.208)
towards 185 pounds, which would make me no longer overweight according to the BMI index, which I don't understand how, because I'm definitely.

Tyler King (27:20.46)
But you're pretty muscular. Like the BMI doesn't apply if you're strong.

RICK (27:24.692)
Okay, well, I don't understand it. But 185 is clearly the like target health weight. And I would, I know what that look, I know what that feels like. And I know, and I want it. So I'm going to continue to just do what I've been doing and take it to 185. And then I won't worry about it anymore. Daily writing and exercise. Up at 5am bed by 9pm. Like that, when I'm doing that, I'm happiest. Yeah.

Tyler King (27:40.298)
Okay.

Tyler King (27:48.844)
Damn, 5 a.m. to 9 p.m. We all have different goals, people. Sounds like a nightmare, all right.

RICK (27:53.995)
Yeah. Yeah. Getting back to basics and the family operation. One particular area about this is like adjusting the family budget to meet our current needs. You mentioned meal planning being a challenge. It is the number one challenge in our household. Sable and I both work. We don't love cooking. It takes a lot of time. But we break it up. But it's the it's the it's a constant like stressor. But also for source of joy.

I don't know how to explain it. but anyway, like one thing we could do with our budget is simplify meal planning with both pre-planning, you know, the, meals so that the decisions already made for us. and then exploring our ways to seek help from family members and services that we pay for. yep. then protect time and space for Sable and I to prioritize our individual personal health, our professional aspirations and our, and our passions. and so like right now, I think like.

Tyler King (28:24.3)
Mm-hmm.

Tyler King (28:38.914)
like that.

RICK (28:51.146)
We're a little too child-centric, in our family operation and we need to continue to take care of our children. I'm not saying abdicate that I'm, what I'm saying is that we need to protect time and space for what makes us great and happy. And, and, and that requires effort. the, next bucket is being proactive in supporting the kids advancement. I've got a couple of things I specifically want to do. I won't go into too many details, like,

Tyler King (29:06.316)
Mm-hmm.

RICK (29:19.084)
Basically, you know, want to Oliver's at an age where skill development's really key. and he's showing interest in lots of different, physical and, you know, like acting and those sorts of things. And so I want to help him pursue those things and develop so that if he wants to do them in any level of seriousness, he's not starting from zero. I want my daughter and I, Avery, we don't, because she was second born, we don't spend as much like natural one-on-one time together as I have with Ollie.

Tyler King (29:45.772)
Mm-hmm.

RICK (29:47.031)
And so I want to be intentional about finding, taking her out of the house, just with her, and doing stuff together. Reese is a junior going, rising senior. want to help her get into a college she's excited about and take her skiing on weekends when I can. And then Porter, my nephew, I want to help him transition to living as an independent adult. He graduates college in April. And I know that's going to be a big life transition for him. And then final personal goal is, be proactive about spending time with people I care about.

This starts with regular quality time with sable one on one and protecting that. I want to make sure we go on to not ever, you know, not more than two, but like at least two really good family trips. Like, Charleston was, I want to support and be present. sable has her, 10 year lucid sabbatical this year, three weeks off. And so I want to, I want to be present and supportive of her doing whatever she wants during that sabbatical and be present with her in that.

Tyler King (30:38.914)
Hmm.

RICK (30:46.226)
I want to see my Lindquist extended family every quarter, which I didn't see. saw them twice this year. and then. Yeah, it's yeah.

Tyler King (30:52.994)
Choice is still pretty good. I mean, not that you shouldn't have that goal, but that's more than most people see their distant family.

RICK (31:01.76)
Yeah, it's not, not enough for me. so I got to figure out how to make it happen. spend time with, leg up health partners more intentionally. Like I feel very, I, I feel like I showed up to every partner meeting without an agenda or any preparation this year. and I'd like to like, make sure that anytime you, me and JD are spending together as much more valuable and, fulfilling. and that may involve even revisiting the cadence and the format for what we're meeting to do.

and then I've, signed up to support my friend Julian with his growth, community, as content chair. I've been doing it for last six months. It's been really fulfilling. and I basically help him manage his podcast, and use AI to like turn it into content. it's mostly like just, it's more advisory. and then I'll speak at his conference. and, it's in the canyons in January.

Tyler King (31:39.934)
What does that mean?

RICK (31:58.479)
That's it. Those are my personal goals.

Tyler King (32:00.194)
All right, that was great. I feel like normally I come more prepared than you to these things and you're about to put me to shame here because I don't have anything nearly that good. No, because a lot of the stuff you said, like, oh, I should have put that on my list.

RICK (32:11.464)
come on. Well, thank you. Thank you for letting me talk. This was, I feel very uncomfortable talking about my personal life like this, but part of why I wanted to do this is this is where I need to actually be intentional and I haven't been as intentional. and I, I will, I think this will lead to like much more alignment and cohesion in the household this year, and a better life for me.

Tyler King (32:37.257)
Yeah. Well, and I like that you took this as an opportunity to like the reason I'm less prepared. not that I didn't spend time writing out my notes that I'm about to share. It's that I didn't actually reflect before them. If that makes sense. I do think like, why do we even have a podcast? No one listens to it. mean, thank you, dear listener. The three of you know, I think there are about 200 people, 200 downloads per episode within the first 48 hours, which is how transistor anyway, we have a few listeners, but

RICK (32:50.35)
Mm.

Tyler King (33:06.4)
The reason we do it because it forces us to think about things that might, you could go a whole year without ever confronting a thing or your podcast co-host could ask you about it and then you have to confront it. So it's good that I didn't do that this year. I didn't really reflect, I don't think. Sorry, but I'm glad you did. Not sorry to you so much as to, well, whatever. Okay, here we go.

RICK (33:26.632)
Don't be sorry.

RICK (33:33.374)
Whoever's not listening. Well, I'll try to throw you a couple of reflective curveballs if I see the opportunity.

Tyler King (33:35.052)
Whoever's not listening, yeah, you can just turn it off right now.

Tyler King (33:41.346)
All right. There we go. One of the reasons I think I didn't reflect much is A, I'm in one of those low agency modes personally with baby stuff where it's just like, you know, it actually I'll talk more specifically in a second. It hasn't been it's actually been really good, pretty easy as far as these things go. So I don't want to make it seem like I'm drowning and struggling to survive here. But I do think it's just like there are things you have to do for a baby that aren't my choice. I don't need to reflect on like

Feed the baby, you know, like, so that's part of it. And then with work also, I did spend some time and again, we'll talk about this later, a month ago or so really putting a plan together for next year. So I have put a lot of thought into that, but I don't think I spent much time like reflecting on how I intersect with work, if that makes sense. But okay.

Personal goals from last year, I'll just run through last year's stuff quickly here. There was baby stuff and specifically, I wasn't exactly worried about, again, like the survival aspect of it, but just like, I wanted to remain flexible, just you can't really plan, just, you know, deal with stuff as it comes. I think I did a good job of that. I kind of made a mantra for myself when Sydney was born, which is the word unflappable, just like, because I think Shelly, my wife, great mom.

great in so many ways, but she can get flustered. And so I kind of viewed my main role as like, when she gets flustered, I need to not be flustered. And I think I did that well. One of them was unflappable. It's not a good word. It's a pretty ugly word and kind of hard to say, but I think it means what I wanted it to mean. Second one was like create space for Shelly to have a life outside of just parenting. I'm giving myself a

RICK (35:16.256)
Unflappable Tyler.

Tyler King (35:34.144)
C- on that. Like, not terrible, but, like, I spent a lot of time... I feel like I give up almost nothing about my personal life. I still go out and hang out with friends and she watches the baby. my parents provide a lot of help. And I, try to offer the same thing. She doesn't... Like, most of the time she wants to go out at night, it's with our friends, not with her friends. But I want to go out with both our friends and my friends, if that makes sense.

RICK (36:02.306)
Mm-hmm.

Tyler King (36:03.562)
That's gonna be a follow-up goal this next year is like try to give her, I don't know what it looks like, but like you need to leave and I'll take care of the baby for a while kind of stuff. And then the third one I had was take advantage of the calm life I've built. That's a very vague goal, but like I think I did this in the sense I took my full three months sabbatical, spread out as I've talked about many times where either day or day and a half off work per week. During that time I really didn't work. Like I spent.

full days taking care of my daughter. I think I did a good job of that. It did affect my work, but I'm in a position where that's okay, and so I'm giving myself an A on that

RICK (36:48.11)
When you say take advantage, like, or create space for Shelley out of just parenting, like, does she want that?

Tyler King (36:57.378)
I think like abstractly she does. think she's more, she has a higher battery for taking care of the baby than I do. Like I love it, but I'm also like after a few hours of it, I'm kind of like, okay, like now I could use a break, know, whereas I think she's more, she has more endurance. I think the big thing is she feels FOMO. Like we have a lot of overlapping friends. When I say I like to go out with our friends and my friends,

RICK (37:09.678)
Mm.

Tyler King (37:26.666)
All of my friends are also our friends. So like, I'll go out with Robert, a colleague of mine. We do a monthly one-on-one for work, but we always do it over dinner. And 75 plus percent of the time, the first hour of it is productive business conversation. And then the next five hours of it, we're She is also friends with Robert and

It's not that she wanted to leave some other night. It's that she wants to be there when I'm with, you know, when I'm hanging out, like in the past pre-baby, I would do that. And then Robert and I would meet up with her and a bunch of other people. Now we meet up with the other people, but she's not there, if that makes sense. Yeah. So, okay. That was basically my only personal goals. I kind of said, I'm having a baby. That's the whole, the whole goal. I do want to give some other updates.

RICK (38:07.17)
Yep, yep, makes sense.

Tyler King (38:22.678)
I like having a baby. I liked it a lot more starting around six months. I feel like newborn was fine, but I don't know. Is that how you felt? Okay.

RICK (38:31.95)
100%. And I I'm I've gotten to the point where I am unapologetic about it. It's like, I do not like I will actually say I don't like the last the first six months. I could I could do without it.

Tyler King (38:43.444)
Mm-hmm. Yeah, for sure. Like, if you compare it to nothing, a three-month-old baby is cute. But if you compare it to an eight-month-old, which is what old Sid is now, a three-month-old is not cute, or fun, or anything. Like, yeah. So, okay.

RICK (38:59.342)
Just wait till you do eight months to like two years, two and a half years. Like it's a whole another thing. Oh yeah, I guess better, way better.

Tyler King (39:02.402)
It gets better to you. Yeah, I many people have told me that I have I just have a hard time believing it because like so yesterday she crawled for the first time and now I'm like, now I have to like worry Prior to this. She was just cute and happy and smiling all the time and she couldn't move But I know there's other good stuff that comes with it I love co-parenting when shit like a weekend when Shelly and I are both around great

A Monday, which is the day I've been taking off work, where I'm just like the parent all day. I still find it fulfilling. Don't love it. I mean, it's fine, but you know, it's work. And then yeah, like I kind of already hinted at, feel like my, like I've been, one of my biggest surprises with this whole thing is my social life has not suffered very much. My sleep has in the sense like I don't sleep in nearly as much and stuff like that, but we...

The grandparents are doing, we're doing overnights at the grandparents house periodically where Shelly and I can both go out and do whatever we want. We're doing other nights where my parents will stay at our house and watch her until we come home so we can do like a dinner. We can't stay out till 3 a.m. But, and like I said, there's the nights where Shelly stays home and I go out. So put those all together and I've, I really feel like I'm getting just the best of both worlds right now.

RICK (40:26.338)
That's awesome. I mean, I, you guys, you're doing great. It's impressive. Yeah. I, co-parenting is great. So the parenting is hard stood out to me as like very true. And I think, I'm going to, I, I would love, I would love that's something I feel like I should have put on my list, which is, being more intentional about co-parenting versus like shift shift parenting. and,

Tyler King (40:28.779)
Yeah.

Tyler King (40:33.548)
Thank you.

Tyler King (40:48.076)
Mm.

Tyler King (40:53.602)
Mm.

RICK (40:55.342)
because I think that's something that's able to struggle with a little bit as we w when I'm up with the kids, she's sleeping or catching up on something or when she's up, you know what I'm saying? and so

Tyler King (41:04.128)
And that stuff's great too though, like as a way to rest and restore. But yeah, it's different when like both of you are in the room with the kid. I don't know how it changes with multiple kids though, where now is it kind of like, you're on that kid, you're on that kid or something.

RICK (41:08.546)
But not as the default. Yep, it's the best.

RICK (41:19.206)
The kids want to be around each other for the most part. mean, it's a little different with Denise and nephew because they are different age. but we're generally when we're co-parenting, it's generally all in the same room, right? Like this is ca it's pure chaos. It's really, it's the best.

Tyler King (41:30.24)
Yeah.

Cool. And then my other personal update is random luck. Someone I work with is very in the local music scene and her friend runs a Halloween cover show. Did I talk about this on the podcast? So at work last year or two years ago, I forget which, we did a mediocre talent show. So was like a talent show, but you're not really trying to impress people. You're just trying to of goof off and have fun. So like one person did pogo stick, know, like kind of stupid skills.

RICK (41:47.97)
You have not talked about this.

Tyler King (42:05.088)
We put a band together for that and played a Dio song, Holy Diver, like an old classic metal song. And it was great fun. We practiced twice. It wasn't good, but we put this band together. Anyway, so my colleague who was the singer in that shitty band was like, there's this Halloween cover band in St. Louis, which apparently, I'd never heard of it. It's apparently this big institution. I think 800 people showed up this year. And it's eight bands, 20 minutes each.

each one covering a different band. And she was like, let's take this cover, this shitty band and go in in this cover show. Now two of the people couldn't do it. So it was two of us from work and two other people. But yeah, I joined a band and we played one show for like the biggest show I've ever played. I used to be in bands back in the day. This is the biggest show I've ever played. Like hundreds of people doing a Danzig cover set. Do you know Danzig? Their main song is Mother. I'm like mother.

RICK (42:58.273)
I don't.

RICK (43:02.286)
I'll have to check this out. I know that song, yeah.

Tyler King (43:03.49)
Dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun-dun- Anyway, yeah, you know that one. You don't know any others. I didn't either. I don't like Danzig, but it was awesome. We practiced every Sunday night for three months and went and played this metal show in front of hundreds of people. was a lot of fun. It was not a competition. It's just a fun and everyone's in costumes and stuff.

RICK (43:10.208)
RICK (43:22.05)
Did you win the competition?

was just for... That's awesome. Did you get encore requests?

Tyler King (43:30.71)
Well, you only get 20 minutes. we actually, we actually only did about 15 minutes because we were like every other band there is like perfect, like semi-pro musicians. And we were only there because Elle is friends with the person who puts the show on. So we did not belong there at all, but, I actually think we acquitted ourselves quite well. People liked it.

RICK (43:49.326)
Do you have a film of this? Will you please send it to me? Show notes, please.

Tyler King (43:51.124)
I do have some film of it, Sure. I don't know about show notes. Yeah, I can put in show notes. Anyway, that was a lot of fun. a high school and college student, did a lot of live music. I was in various bands, big part of my life. Like so many things when you're a kid, as soon as you become an adult, just completely stopped. I stopped playing water polo. I stopped being in bands. Those were my two main things back then. Really fun to just kind of resuscitate that.

I don't want to be in a full-time band, but like one show per year would be awesome. So maybe it'll happen again next year. We'll see.

RICK (44:25.454)
That's awesome. Yeah. That'll tell you how you did if they invite you back.

Tyler King (44:30.804)
Yeah, they said they liked it. I don't know. Yeah. So yeah, that was 2025. Personal goals for next year. Yeah, transition back to full-time work. I'm sending this as a personal goal, not a work goal, because I'm not worried about will I be able to work five days a week? That's what I've done my whole adult life. It's just like, what will parenting be when I'm working five days a week?

RICK (44:34.412)
Good job!

Tyler King (45:00.29)
So I'm not worried about it per se, but like big change coming in early January where, because not only am I going back, but Shelly's going back to work full time as well. So we're going to, my mom's taking care of Sydney two days a week. We are getting a nanny two days a week. Shelly's off on Fridays. So it'll be a big change. Hoping that goes well. Yeah, thanks. We're going to daycare at some point, but not quite yet. Yeah.

We've been having some kind of personal finance conversations, Shelly and I. This is like such a champagne problem. Like, I don't know how to say this in way that doesn't make me sound like an asshole, but like, we feel like we have too much money and we feel guilty about it, kind of. We're not like rich rich, to be clear. I pay myself $250,000 a year, but Shelly makes money and she inherited a little money. we are...

high upper middle class or something like that. But like, A, I feel like spending on yourself is good to a point, but like there's a point where you're like, I feel gross with the level of luxury. Like there are people struggling and I just, no one should be as comfortable as I am kind of. And we all know that raising your kid in an environment where they experience the wealth is bad for the kid, right?

RICK (46:08.27)
Hmm.

Tyler King (46:25.93)
Or I think we all know that. Rich kids suck. Do you agree with that?

RICK (46:33.422)
That seems to be a trend. I don't know that it's that simple. Yeah. Yeah.

Tyler King (46:35.38)
Okay. It's possible to raise good rich kids, but I think it's much easier to raise good middle class, upper middle class kids.

RICK (46:44.386)
There's I think a lot of kids who didn't grow up in a rich household who who suck too. Yeah

Tyler King (46:49.542)
for sure. Yeah, I'm hoping to avoid that too. But like, for example, if I can afford to fly first class, even with Sydney, which I should say I never flew first class in my life until this year, but now I'm like, I'm flying first class. Yeah, bitch. I don't want my kid to grow up being used to that level of luxury. That's crazy. I think that's my opinion.

RICK (47:14.358)
What is what is what are you scared of? guess is it just the title meant?

Tyler King (47:17.238)
just getting spoiled, just classic, I haven't said the word spoiled, kids get spoiled. They get entitled. They struggle to adjust to reality. Yeah. And then it's like, okay, well, either I'm giving them enough money to maintain this lifestyle forever, or they'll be miserable. it's just not, and nobody needs to live like that also. I kind of believe in a version of capitalism where you eat what you kill. Like if you're successful,

RICK (47:26.636)
Reality.

Tyler King (47:43.7)
you deserve some benefit to that success, but like my kid isn't successful. She needs to go earn it. That's my belief.

RICK (47:49.878)
Yep. Well, you can always buy a first class seat for yourself and put the kid in the back of the plane.

Tyler King (47:55.222)
right by herself. Yes, that'll, she'll learn quick that way. Anyway, the first class example is contrived because I wouldn't, I also wouldn't do that. wouldn't for price reasons, but anyway, we've been having some conversations about that. And so one of our goals, one of my personal goals this year is to just like figure out how to balance, like what type of

RICK (47:59.727)
You

Tyler King (48:22.338)
Financial exposure, do we want Sydney to see and do I even without Sydney, do I feel comfortable with personally? like, I won't get into all the specifics, like we shall and I recently significantly increased the amount we're donating to charity. It's still not as much as it should be probably. We put limits on like, we will do this like it's okay having someone cut our lawn, but we don't want her to have a full time nanny like that type of that type of thing. So.

RICK (48:49.848)
Mm-hmm.

Tyler King (48:51.81)
I know, I probably rambled too much about this, but that's one of the things on my mind. And my.

RICK (48:56.046)
And just to make sure I understand it's basically being intentional about where you're spending money and also where you're not.

Tyler King (49:03.082)
Yeah, yes. And like having a system, so why is this a goal? It's not just like a topic, I mean, it is a topic I'm rambling about, but the goal is like, at the end of the year, I don't want to have to question every single decision. Like right now, every time we're like, should we buy this thing or should we subscribe to this service? We're kind of like, do we feel comfortable with this? Yes or no? I just want a system where we're just like.

RICK (49:27.618)
You want, there's a decision made for you.

Tyler King (49:29.408)
Yeah, we've set boundaries. Which side of the boundary line is this on? That's the yes or no. That's what I

RICK (49:34.158)
Yep, Well, you can always join the LDS church, which takes 10 % of your income with tithing.

Tyler King (49:40.832)
Yeah. You know, that's funny. That's actually, we were discussing how much should we donate and I was like, well, Mormons tithe 10%. And we were just like, all right, 10%. That's the number. Self-tithe. Yes, exactly. And then also related to this, I need to get a will and trust set up. I don't have any of that stuff.

RICK (49:52.962)
We'll self-tie it. Yeah, that's good.

RICK (50:04.544)
I did that. I know the feeling of like, you got to take care of your legacy. And if you don't have it, it feels weird. But you don't care about it before you have kids.

Tyler King (50:13.802)
Yeah. Right. Well, and I think like if I die, there are laws that will would the will will say do what the law says to do. Like it just simplifies it. I don't think like all your money vanishes magically if you don't have a will. But yeah, still worth doing. OK, and then my final personal goal. Sorry, that was incredibly boring. Man, I should have left that one out. My next personal, you know, the will and trust, though, the whole personal finance thing.

RICK (50:23.425)
Yep.

RICK (50:36.662)
The will and trust? No, that's a real thing.

No, that's super interesting. I think Sable and I are still like, it's just trying so hard to survive. I think she actually thinks more about this area than I do. I would say I'm not as subscribed to worrying about these things as you are or as Sable is. I'm more like, if I have a connection with Oliver and I teach him how to be resilient,

Tyler King (50:50.923)
Yeah.

RICK (51:10.606)
And he, he learns how to pick himself back up and what a good job well done is and how to be nice. Like those are the things that I can teach him regardless of the financial decisions that we make. Um, but I, but I, but I, I can see your point where it's like actually, uh, a life of luxury is counter to resilience. Um, and it's, there, you know,

Tyler King (51:24.332)
But you-

Tyler King (51:34.154)
It's partially that, but also isn't, I think a difference between you and me in terms of how we think about politics and stuff like that is I just don't think these things can be separated. think if you say I deserve or I'm comfortable with a kid having a $10,000 plane ticket with a lie flat seat, so they can be comfortable for six hours instead of that like.

that money going towards something else. That is like implicitly a belief. That's not just material consumption. It's, think I deserve this and someone else doesn't, kind of. That's how I think about that and why I feel more conflicted than you do, I think.

RICK (52:20.984)
So you're saying that you want to model a certain frugality with money and thoughtfulness about money so that your children learn sort of that belief as well.

Tyler King (52:37.046)
Yeah, this is also why I think I'm, even though I'm a complete all talk, no action when it comes to politics, I do care about it in the sense that I think neutrality is like such a privilege that shouldn't, like none of this stuff affects me, but I think it's a statement to say it doesn't affect me, so therefore I'm neutral on it, you know?

RICK (53:01.506)
Have you read the psychology of money?

Tyler King (53:04.098)
No, who's it by? Okay, no, I don't think so.

RICK (53:05.352)
Morgan how I don't have his last name household. Anyway, he teaches he broaches the subject, you know, in a very interesting way, and talks about how everyone's irrational about money. Because of it, and it's, it supports what you're saying, but it also counters what you're saying. What he's saying is no one's psychology about of money is right or wrong. It just is based on how you're raised.

Tyler King (53:19.394)
Mm-hmm.

RICK (53:34.707)
and what you experience, what your past, your current psychology of money is based on your past experience with money. and I think what you're saying is you want to be intentional about the experience you present your children with money so that you influence the psychology of money they have as adults. And I think that is a very, I think that's a very, admirable and smart thing to do. And I think I need to do that too. And, I am not doing it.

Tyler King (53:52.32)
Yeah, okay.

Tyler King (54:00.726)
I like that. That's a much, much less judgmental way of saying what I, what I said. Yeah.

RICK (54:04.846)
Yeah, well, I mean, at the end of the day, like you have a belief, right? you're, yeah, values. Yes, exactly.

Tyler King (54:08.618)
It's values. You're passing values down to your kids and this is one of those values. But I'm also selfish. We're all self. It's like I want to be selfish and greedy and I want to be a good person. And anyway, OK, my final one, I and I'll keep this quick. I have like very like an AI type goal for professional stuff. I'm not going to set this as like a goal where I definitely want to get this done, but like a nice icing on the cake at the end of the year would be. I'd like to be able to say I vibe coded.

RICK (54:16.908)
Yeah.

Yep.

Tyler King (54:38.73)
Just a personal app to do a thing that I want. So let me give you a specific example on Mac. Their window management sucks. I've I'm two years and I still haven't gotten used to it. There's a program called rectangle that makes it a little better, but there's one specific thing about rectangle. If I hold control alt and hit enter, it maximizes the screen, but the size that it maximizes to is different. Whether this one setting is on or off, I just want to make an Mac app that overrides that one hotkey and makes the window this.

the window, size I want it to be. There are a million of those and it doesn't have to be that specific one, but I think it'd be one of the themes that I like about AI discourse right now. They were just talking about this on the mostly technical podcast is that a lot of things that didn't used to be worth it are now worth it because the amount of effort has decreased. And this is a good example of that of like, I'm not going to go build my own app for this little tiny thing, but if I can just tell

Claude code, hey, go do this and probably spend a few hours figuring out how to actually bundle it up and make it an app that I can install. It turned from not worth it to worth it. And I'd like to take advantage of that a little bit this year.

RICK (55:49.167)
I like that. It's like, it's almost like AI has opened up the long tail of apps. Like Amazon opened up the long tail of content and books and the Google, you know, did the same thing. Um, uh, that's a very interesting potential opportunity.

Tyler King (55:58.7)
Mm-hmm.

Tyler King (56:03.244)
Yeah. I wouldn't, no, I wouldn't even give it away. Just use it myself and never even tell anyone about it. Yeah. It's not even about, I think I used to have this attitude of like everything has to be productized or it has to be a learning experience or whatever. What I'm kind of saying is it might be easy enough. I just want my problem solved. Exactly. Yeah. I won't be able to help, but tell people about it. Actually, I'm lying. I will.

RICK (56:05.826)
Will someone pay for this or you can give it away or you just gonna use it selfies it. All right. And learn learn how to build a desktop app.

RICK (56:22.67)
I just want my problem solved. Yeah. That's very cool.

RICK (56:31.446)
Yeah, but you don't know what you don't know is like, what this this is a good thing to spend time on, because it has so many like, open ended possibilities of where it could go. And it's all the problem. Yeah.

Tyler King (56:40.33)
Yeah, right. It creates serendipity potentially. All right. We are one hour in and we're done with our personal updates. We've got two hours booked here. Let's see if we use the full time. I'm guessing professional will go faster, but do you want to take it over for professional goals?

RICK (56:50.126)
You

RICK (56:54.854)
yeah. Yeah. Yeah. Sure. I, so I listened to the episode last year on professional and when I got to professional, I was like, just so know, I haven't really thought about this. I'm just, and, and, you know, we'll figure this out, but here's what I think. So what I said was I don't know yet, but most likely, two X revenue, maybe less make sure JD's role is sustainable and make sure the business is properly financed. I think I've done.

So we ended up settling on a 50 % growth goal. uh, uh, you know, getting JD to his target comp being the two primary goals. And then the third being making sure we don't run out of money, which is kind of always the goal. Um, and we did all three of those things. Um, I'll talk a little bit about it, but, I just want to say like in general, my professional goals took a backseat to personal stuff in 2026. So I don't feel like I did it. I did a lot of stuff.

professionally, but I don't feel like I did a lot of stuff well. And so we'll just, I'm trying to be positive, but like at the same time, I'm like pretty negative about my professional contributions.

Tyler King (57:51.564)
Mm-hmm.

Tyler King (58:01.708)
Well, let's, okay, let me put a slightly more positive spin on this. Like this is why calm companies, startup to last, bootstrap, whatever you want to call it. This is why it's a good model. You hit all three of those goals through really no effort of your own, right? Like, now, I mean, maybe that's just an argument for higher good people, but you set up a business that could achieve your definition of success.

even in a year where you're highly distracted by other stuff. maybe that's, I'm not saying you should feel good that you didn't do more for the business, but you should feel good that you created a business that could still succeed despite those challenges.

RICK (58:42.008)
Thank you for saying that. And when we, when we talk with JD as part of our, what, what, what's like it's a goal. This makes more sense. Our creative exploration. Like I would love for you to bring that perspective. I definitely feel guilty about not contributing more to the business. just do, I don't feel like, I feel like I tried to do things. I tried to, I said I would do things that I, that I still haven't done and that doesn't feel good. I probably shouldn't have said I would do those things.

Tyler King (59:06.324)
Yeah, okay, right. Sorry to belabor this. Probably the problem is saying you were gonna do it, not that you didn't do it. Yeah.

RICK (59:11.63)
Correct. Yep. So I going well at leg up health JD is now this monthly target comp and we hit our 20k MRR milestone mid year, which was the annual goal. What's not going well is, I don't know if I think I've talked about this on the podcast, but the Obamacare subsidy expiration and the way that the government handled that expiration through the

you know, budgeting process and shutting down the government was really, really bad. It led to a lot of lost consumer and employer clients. and as a result, we'll end the year below the 20 K goal because open enrollment usually is an 80 % of our growth. And it was actually negative growth this year for us.

Tyler King (59:48.833)
Hmm.

Tyler King (59:54.946)
Is JD still at his target comp after that?

RICK (59:58.477)
Yes. Yep. we're not, it'll be about 19 K. So we'll miss it by a thousand bucks, but, that's conservative estimates. So it could get better between now and February, but, it's pretty.

Tyler King (01:00:11.106)
I think those people have to come back. This sucks in the short term, but those people aren't lost customers forever.

RICK (01:00:18.53)
I think so too. think you're right. and we could have, I think when we reflect, go, we could have probably saved some of the employers, but we were just like, this is where, this is where I like, I feel like I probably wasn't, this is the stuff I could have been thinking about more like where, with what I was spending time on. If Jay's in the weeds executing, I could have been more like, okay, here's our risk mitigation strategy. And so I think we tried to grow when we should have been playing more defense. and, anyway,

Tyler King (01:00:37.92)
Mm-hmm.

Tyler King (01:00:46.742)
Okay.

RICK (01:00:47.596)
Lessons learned. but, but we got punched in the face and up enrollment this year. And, I feel really, I mean, at the end of the day, think JD did everything he could to, this is not an execution issue on his part. Like he, did everything he could. And I'm, I can't believe he's still breathing after what he dealt with, because if you imagine this, there were so much change and uncertainty, imagining like what normally would take on average five to 10 minutes per customer, for, for, for consumer client taking an hour per client, because there's like what

I don't understand what I don't understand. I can't afford this. What are my options? Well, let me explain this and put asterisks on every other option that you have because it's not real health insurance. anyway, it was

Tyler King (01:01:20.994)
Mm-hmm.

Tyler King (01:01:29.058)
Yeah. And when they leave as a client, it's just because they literally can't afford to buy the thing. Like, what are you going to do about that?

RICK (01:01:35.85)
Anymore. Nothing, nothing. Exactly. Um, so anyway, uh, I'll shift to windfall. Um, what's going well is, uh, we raised a $65 million series B from Morgan Stanley. Um, I don't know if I announced on the podcast or not, but, uh, that was really, really good for the company. It was really, really good for my friends, uh, who are to the founders. Um, and it was also good for employees who've been there a while, um, like me and, you know, so that was a kind of a nice financial.

outcome I'm still learning a ton, at windfall about like high growth startups and like moving fast, and making meaningful contributions. which is a good sort of piece. it's a good, like for financially it's been, what falls been terrific, both from a ongoing comp perspective and then a, you know, the, the, the, the, the recent race, what's not going well at windfall is that I'm still very much in the weeds. My role is.

playing a Swiss army knife. I have active stints right now in marketing and customer success, which is outside of my core job. but like, it's also very fulfilling cause like I get to work on lots of different problems and learn lots of different things. but like my core team in rebops hasn't grown enough to allow me to scale myself. So I go from like high level work outside of my team to like micro work within, in my team. And it's like very hard context shifting and stressful.

And then the other, the thing, and went, fall, it's not going well. And I feel this very, very acutely is that AI has created some chaos for me at, at, work in the rev op space revenue operation space. and as I'm trying to figure out where my time should go, like my job's evolving, and no one, there's a lot of it. It's hard to tell like what's hypothetical out there versus what's the new sort of standard for someone in my job. And so it's, I'm

It's, um, you know, what is true is that, you know, there's kind of one on one side, it's like, can't argue that AI provides a massive opportunity for leverage and that from a go to market perspective, revenue operations, my job is at the center of that from a tooling and configuration perspective. But at the same time, I'm like, this is not necessarily real. This is all hypothetical. Um, and where I, where I feel very weak is when someone is telling me this is possible, we can do this.

Tyler King (01:03:53.142)
Mm-hmm. Mm-hmm.

RICK (01:04:02.626)
for you, my ability to dig in and actually say, is that possible? Like technically, like I feel very weak and I have to, I feel like I have to try it in order to learn it versus being able to like use my knowledge to say, no, no, that's actual, we're not there. and so anyway, I,

Tyler King (01:04:06.658)
Yeah

Tyler King (01:04:18.326)
And I feel like your nature is like whatever the opposite of a skeptic is, like you are very positive and like thinking about things going well much more than you're thinking about things going poorly. I think I'm the opposite. If someone pitches me on our tool can do this, I'm like, bullshit, prove it. I think your nature is to be like, great, I see all the opportunity there, right? Do you think I'm right about that?

RICK (01:04:40.396)
I think in general, I'm pessimistic on AI though. And I would say I've, I've gotten some egg on my face trying to do AI and but I feel but it's funny. I think this is the one area I feel pessimistic about let's just say it which is counter to my normal. But the pressure from the industry and you know, the industry on the business to make this be optimistic about this is so high. And so it creates a lot of

Tyler King (01:04:42.879)
Yeah.

Tyler King (01:04:56.928)
Yeah.

RICK (01:05:08.618)
a lot of like, okay, how do I prioritize this, but also keep the trains running the old way, you know, it's, it's very, and it's, it's happening so fast. So that's, it's, it's, it's not going well. And that the sense that it's like, I'm reacting to it, like that theme of reacting, but, at the same time, it's very interesting, you know, and the opportunity there's, I'm optimistic about the long term opportunity.

Tyler King (01:05:23.094)
Yeah.

Tyler King (01:05:32.418)
Can I pause you real quick? Since we're going long here, that is the sound of my second Dr. Pepper opening.

RICK (01:05:33.708)
Mm-hmm.

RICK (01:05:38.808)
Well, I wish I had a coffee machine in here because I'm out of my cup of Joe. Guess I'll switch to water.

Tyler King (01:05:42.501)
I anticipated this and brought two mini 7.5 ounce cans of Dr. Pepper, which means I just spent an hour and seven minutes drinking my first seven and a half ounce can. Okay, go ahead.

RICK (01:05:52.943)
Good. I'm glad that I'm glad you did that. I'll shift to like my goals for 2026. This is going to be pretty short. Feel free to ask questions, but like I've got four professional goals for 2026. And if I get two out of four of these, it's a win. like it's okay, our type goals. So I just want to be very clear. My first one is to outsource delegate or automate recurring tasks that I no longer value doing.

Tyler King (01:06:09.004)
Mm-hmm. Mm-hmm.

RICK (01:06:20.174)
and or others don't value me doing. And I, that could be anywhere in life. Uh, the second is try to grow leg up by 50 % or more. Um, but do it in a way that we, you, me, JD are all excited about. And this starts with an exploratory session or two or three. Now that we are default alive with JD's target based salary covered where we go, what do we want to build?

Tyler King (01:06:21.868)
Love that.

Tyler King (01:06:48.598)
Mm-hmm.

RICK (01:06:49.746)
And I am, I don't know what that looks like because I haven't had those conversations with you all. But I think like, I think it's within our power to grow the business by 50%. We've proven that ish. And I think that we could focus or on area we could we could choose to do things differently moving forward if we wanted to. And I'm curious where some creative exploring would take us.

Tyler King (01:07:12.404)
It sounds like you have some thoughts on that, and I'm not asking you to share them right now, but you seem to be like, you wouldn't say it that way if you didn't have some ideas, right?

RICK (01:07:22.122)
yeah, you I mean, we could spend two hours talking about this, right? I don't want to I don't want to poison the well. Okay, yeah.

Tyler King (01:07:24.554)
Yeah, yeah, okay. I'm not asking for them. Yeah, I'm just making, okay. So my next question, like, when are we gonna talk about this?

RICK (01:07:33.507)
That's what I want to talk to you about. I don't necessarily not on this episode, but like, I don't think our partner meetings were very productive last year. I think I was a big part of that. Format's part of it. The stage of the business, we did nothing really mattered other than getting JDS target comp. Now that JDS target comp is like, okay, now what do we want to do next? You know? And so I don't know, but like, I'm happy to do whatever y'all think is best, whether that's having some,

Tyler King (01:07:37.516)
Mm-hmm.

Tyler King (01:07:41.621)
I agree.

RICK (01:08:03.32)
time to talk together, to walk together to ski together, I don't whatever y'all want to do. And yep.

Tyler King (01:08:09.035)
Well, here's my proposal. Our next partner meeting is January 5th, so it's very soon. And they're an hour and a half. I'd say, tell JD and me before that, we are only talking about this VisionQuest thing. No updates on the business, no talking about pipeline problems or what should I do with this client or whatever. And dedicate the last 30 minutes of that to planning the next meeting or like...

RICK (01:08:14.211)
Mm-hmm.

Tyler King (01:08:38.048)
I feel like a problem we run into with the partner meetings is those are the only times we talk. I know you talked to JD separately, like, so what the business does is constrained by what we talk, like how much time we have in those meetings. It's kind of a forcing function because you're so busy and I'm very part-time. We just need to make the time to talk and it could wait till January or till June if we're not careful.

RICK (01:09:05.728)
You're saying that basically reformat the partner meeting to be the vision quest and let that play out for a couple of months. And if it doesn't go anywhere, do more.

Tyler King (01:09:13.922)
I'm saying do it for the first one, but the second meeting should almost certainly not wait a month. I don't

RICK (01:09:20.398)
I see. I see. Okay. noted and I think I 99.99 % agree. I just want to think about a little bit more. Um, but yes, I think you're right. Um, so anyway, um, I think like, I want to just take a second and say thank you to JD. Thank you to you. It feels very good to have leg up health here. Um, where I think like

Tyler King (01:09:22.026)
But that can be the we can get started there.

Tyler King (01:09:29.41)
Yeah, Cool.

RICK (01:09:51.309)
we can decide where we want to go from here. I felt like last year we were constrained by, I'm sorry, but we can't really be that creative. We've got to march and push towards getting JD to start comp because we don't get there. Like we don't have anything.

Tyler King (01:10:03.68)
And despite the things you feel guilty about, until open enrollment, which was totally outside of anyone's control, last year was great. Like JD hit a kind of growth flywheel last year that had never happened before. And it's better in every way. It's higher margin, like employer customers instead of individuals, much more selling our proprietary tech rather than just being an insurance broker. Like last year was a great year until the unavoidable Obamacare stuff.

RICK (01:10:09.838)
Mm.

RICK (01:10:32.76)
All right. Move personal web. My third goal is move my personal website to flow web flow and get back to consistent content production. I want to read 10 really, really, really, really good nonfiction books and publish notes on them. I picked a few topic areas that I'm interested in and I'm going to like my main goal is to narrow the topics I'm interested in and go deeper in those topics. I've got four or five topics I've picked from parenting to AI to

Uh, uh, money management. Um, and then, uh, my, my final, my fourth goal is to experiment with AI to generate one additional revenue stream. Um, and it could be, it could be in the health insurance space. I hope it is like, or it could be helped. Like the area is the problem that I really resonated what you're doing with vibe coding, uh, with your, uh, command, uh, shortcut hotkey is very similar to this and that.

There are problems that like up health experiences that I believe AI could help solve. And I would like to use that to learn more AI applications, but also solve the problem for like up health. could be distribution. could be automation, that kind of thing. like a chat bot. and so those are the, that's the area that I'm sort of constraining this, but I, I just want to play a little bit and, and, and, and, this would be a fun sandbox. This is, this is my least important goal by the way.

Tyler King (01:12:01.228)
I think if you wanted to, you could combine goals three and four together. Rather than moving your personal site to Webflow, build a CMS for yourself with AI. I realize you're not saying specifically AI coding, you don't need Webflow anymore in an AI era. It wouldn't generate revenue probably, but that could be a project.

RICK (01:12:25.112)
That's interesting.

Tyler King (01:12:28.802)
Something to think about.

RICK (01:12:29.74)
Yes, sir. Anyway, my biggest worry for 2020, we have a biggest worry this year?

Tyler King (01:12:36.994)
Did I do one? No, I didn't. But I mean, it's fucking obvious. It's got to be AI for everyone, right?

RICK (01:12:41.356)
Yeah. Yeah. Missing the AI training and getting left behind is my biggest worry.

Tyler King (01:12:44.758)
Yeah, it's, mean that plus it's missing the train plus does it destroy all the jobs? it? Yeah. Like even if there's all these people, I'd say I'm around the middle of the pack in terms of AI adoption. I don't think I'm ahead. I don't think I'm behind. Even the people who are ahead could still get crushed by it. Right. there's a question of, it useful? But there's a separate question, whether you think it's useful or not. There's a question of, it good and is it good for you?

RICK (01:12:50.082)
Getting right over by the plane.

Tyler King (01:13:13.642)
And no matter what you do to adopt it, it might be bad for you. So yeah, that's gotta be the biggest worry, I think.

RICK (01:13:21.836)
Yeah, I mean, like a snowstorm might be bad for you, but you can't make the snow not come.

Tyler King (01:13:26.658)
Right. Cool. I like it. I'm trying to... Sorry, I'm just looking one more time at your goals. I especially like... Yeah, you kind of listed these in order of priority. Yeah, your first two, outsource delegate or automate recurring tests that I no longer value doing and others don't value me doing. That should be everyone's goal every year, I feel like. I believe I made that goal a year or two ago and 25 % did it. It was still good.

RICK (01:13:55.536)
Yep.

Tyler King (01:13:57.417)
Okay, cool. So for me professionally in 2025, my goals that I stated were don't worry about growth, focus on input, not output. The logic behind this being like, we have a plan. I feel good about the plan, but I don't think the plan will show results in 2025. I think at the earliest it be 2026 and maybe even 2027. So as a result, I just have to stay motivated to do the work and not worry about seeing results. I think I did that great.

We are still just fully 100 % plateaued. It'd be harder if we were dropping. I mean, technically we lost users, like less than 1 % of our revenue. If we were like losing revenue in a meaningful way, it'd be hard to just be like, well, you just got to stick to the plan, right? But as long as we're plateaued, think I'm just, I feel good about the plan. I'm not really looking at the numbers that much. I think I did that one. On the product side,

I said, I want to tie off the big 2024 projects. Those were forms and automatic email logging. Both of those shipped. Well, it's hard to say when they like they launched to customers early 2024. I'd say we stopped working on them around spring. Sorry, early 2025. We stopped working on them around spring because the normal pattern like you ship it, but then you've still got a handful of things you want to do to improve before you move on. So we didn't really start on the next round of things until like May ish.

this year. So we did that. The next goal was definitely ship Kanban in a mobile app. And then the stretch goal was ship one other big thing, which could include automations. Those got flipped. We shipped automations earlier this month. Kanban and mobile app, we made a lot of progress on. Neither of them are shipped yet. think there's nothing special or interesting to say here. Just things take longer than you think.

Let me talk about an insecurity I have of like, bet, I think listeners are thinking this when they hear me say this, but I'm not sure. Which is like, why does it take so long to build a Kanban board? Have you ever thought that? Yeah.

RICK (01:16:04.972)
I was thinking that. Why does it take so long to build a Kanban board?

Tyler King (01:16:11.194)
Yeah, let me ramble about this for a second. So A, it's possible like we're just not as productive as other dev teams or whatever. We're not using AI well enough. think that's actually, like, I do think we, that's gonna be one of my goals, but I actually think we've done pretty good on it. I think in our world, I say our world, you don't follow bootstrapping stuff that much, but like a lot of our listeners are also listening to the panel.

with Justin and Brian, they're listening to mostly technical with Aaron and Ian, they're listening to those types of things and following those types of people on Twitter. And when you follow them, someone just adds a con bon board to their app over the weekend. And I often hear that and I'm like, what the fuck, what's wrong with me? What's wrong with us? I think most of the answer to this, if I can be defensive for a second, is it's just very different building a highly constrained

sort of prototype style app with no users and no real usage versus building like a production CRM feature with 25,000 users and some of those users having a million records in their CRM. A simple Kanban board would take a weekend if you said there's no filtering, because like one of the big projects,

All of our filtering happens on the backend on the server. We have to rebuild all of that logic in the front end. cannot build a responsive Kanban board if you don't have front end filtering. And there's a lot of really complicated filtering options. One of them is like, if two people are looking at the same board and one moves a card, it has to move it on the other board. That's no problem. But what if one has a filter applied and the other doesn't and you move a card, where does that card go in the filtered view or vice versa? If you have a million leads, which you may think nobody has a million leads. Yes, they do.

you can't load that on the front end. now you need to do lazy loading on rows. need to do lazy loading on columns. How do you sort stuff? If you don't have all the data loaded in the front end, but you're doing front end sorting, you have to aggregate these numbers to say, well, here's the total value of this status in the pipeline, but we only have the first hundred on the client. So the backend had to get all million, but the front end only got a hundred, but it got the aggregate number for all million and on and on and on. I think our world.

Tyler King (01:18:27.01)
talks about new projects and prototypes and all that so much more than the actual reality of building software for customers.

RICK (01:18:37.218)
counterpoint to you, could you not release a imperfect Kanban board as a beta product and get it shipped as a skateboard version versus a Mercedes version?

Tyler King (01:18:39.02)
Mm-hmm.

Tyler King (01:18:57.024)
I mean, kind of, but...

Not r-

RICK (01:19:01.006)
Like, couldn't you create an environment within your app in which you could release the most basic form of combine just like a

Tyler King (01:19:08.524)
Does that achieve business goals for us? Like when a new user signs up, do they get this barely working super limited convo?

RICK (01:19:18.978)
with a beta, you know, sort of flag on it, why not? That would give you more feedback on what their actual usability is versus having to assume it. Now, nothing you said is something you shouldn't build. right? Like filtering on a Kanban board, is that a must? Especially if you have a million records. Anyway, I didn't mean to, yeah.

Tyler King (01:19:28.468)
Yeah

Tyler King (01:19:35.21)
Yeah, I hear you. could have shipped it. So we are doing what you're saying. like, it's probably going to start data testing around next month would be my guess. And then we're probably going to work on it for another three or four months after that. so it's not like we're waiting for everything to be perfect, but we are waiting for like, maybe I'm totally wrong about this. think when you have like standards are high for CRMs, like we're not, this isn't 2012 when you make something and you're the first person to put it online and everything else is some like,

$100,000 enterprise on-prem thing. There are a lot of CRMs out there that are really good, that have Kanban boards that actually support all this stuff. If you're evaluating a product and, it has a mobile app, but the mobile app sucks and it has a Kanban board, but the Kanban board sucks and it has automations, but the automations suck. Is that better than not having those things? I guess, I don't know.

RICK (01:20:24.034)
I'm, this is making me think about the, one of the themes that you, that I had for my personal goals, shifting from a strategy of playing it safe and reducing risk to taking smart risk and being okay, looking a little foolish. This feels like this could potentially fall in that category of like, you're maybe playing it too safe.

Tyler King (01:20:29.954)
Mm-hmm.

Tyler King (01:20:39.436)
But risk needs upside. If we're gonna work on it either way, like what's the upside?

RICK (01:20:41.646)
If there's no upside here, if there's no upside here to release it sooner and get.

Tyler King (01:20:47.222)
The upside is like, yeah, is like three months worth of free trial users see this feature that they didn't see. That's a little upside, but it would have to have a huge impact on conversion rates for that to matter a lot, I think.

RICK (01:21:03.544)
But what what's the downside risk? Like, what are you actually concerned about people people

Tyler King (01:21:06.626)
In the opposite direction that it actually hurts conversions because all these features suck

RICK (01:21:11.886)
a bad trial experience leads to a lost customer.

Tyler King (01:21:15.566)
Given that our whole brand is like not very many features, but it actually works. I'm I acknowledge I'm being a little defensive. I don't think you're exactly wrong. I just don't think it makes that big of a difference. Like where the difference would be is if it could if you could if what you said would have cut the total project size in half and then we could stop, that would make a big difference because like over time, the time savings compounds. But if it's like it's still going to take all that time, we just got to ship it.

a little bit earlier. I don't know.

RICK (01:21:46.297)
I think you said something different than what you said originally just now, which is it's not about stage of business. It's about your positioning as a less annoying CRM, as much as it is about your stage of business, compared with the bootstrapper. Like you, you'd made a point. Yeah. So it's two, two different things that I think are, add up to a reason to be very risk averse here.

Tyler King (01:21:49.781)
okay

Tyler King (01:21:59.446)
I think that's two different things.

Tyler King (01:22:06.658)
Sure, but sorry. What I mean is that our brand is why we don't ship it early. Our stage of business and the type of product we make is why it takes so long. Like Ian Landsman, I know you don't listen to mostly technical. Ian Landsman is building a podcasting, a tool to help podcasters organize their podcast and it's got a Kanban board in it. But it's like, if you and I need a Kanban board to keep track of our topics, you don't need any filtering. You can just assume there's never going to be so many cards in a single episode.

RICK (01:22:16.152)
It's hard.

Tyler King (01:22:35.948)
that you can't just load them all on the front end. That's the type of thing I'm saying where, yeah, you could build that really quick and just ship.

RICK (01:22:42.114)
Yeah, there's not, the record complexity is not there.

Tyler King (01:22:44.714)
Yeah. Also, people spend... Yeah, sorry, go ahead. Yeah, I know this isn't the point.

RICK (01:22:46.786)
Anyway, your point, I just want to make sure like, there's two things here. Like I could argue against like worrying about how hard it is and shipping it in phases. But like when you add in like actually our brand positioning relies on us not doing stuff like that, then it's like, I can't argue with you anymore.

Tyler King (01:23:06.398)
Yeah, it's a bit of a cop-out, of course. Like, anyone could say that.

RICK (01:23:08.14)
Yeah, yeah. But it's true.

Tyler King (01:23:12.714)
It is true and again, at the end of the day, it doesn't make a big difference whether we ship it early. It matters how long the total project takes, I think.

RICK (01:23:21.806)
And like, but this also just, I don't, I know we're going down a little bit of a rabbit hole here. If, if, if shipping combine early and making faster progress on it isn't meaningful to the business, why are you working on combine in the first? I don't mean to like open up a of worms here, but like, if it's not, if it's not urgent and important and impactful to get this thing out, then why I work on it at all.

Tyler King (01:23:27.19)
You

Tyler King (01:23:42.87)
No, that's a great question.

Tyler King (01:23:49.174)
Well, the hope is that it will so. Five years ago I dreamed of we're going to build this feature and that this is the one right? I know there is no one feature. There's no feature that when we ship it, everything is going to change magically. The hope is so I'm. I forget if yeah, I have this in just a second while say it right now. I was doing some digging this the hope with.

RICK (01:23:58.723)
Yeah.

Tyler King (01:24:15.648)
The CarPlay strategy, is what this is all a part of, I'm not going to rehash what I mean by that, but the hope is we build the features that will increase the trial to paid conversion rate. It's not going to increase the size of the funnel. It's not going to necessarily reduce churn. It's going to increase trial to paid conversion rate. We used to be at 32%, 32 % of our trials paid. Over the last five years, that dropped to 27. If we got back to 32, that would fix our growth problems.

Probably the actual fix is going to be a combination of things. We need to increase our funnel a little, we need to reduce churn a little, et cetera. But it could happen entirely through this one thing and not like some unrealistic number, but just getting it back to where it was. Will these features do that TBD? But even if they do, each feature, we're talking about a 1 % difference. And a 1 % difference over years combined with five other features that make a 1 % difference each matters. But getting

a 1 % difference three months earlier doesn't really matter. Yeah.

RICK (01:25:16.494)
doesn't make a Yeah. Nope. I think you had to ask the question. I think you've got the right answer.

Tyler King (01:25:22.176)
Yeah, I appreciate the pushback. Okay. So maybe I'm just making excuses. These things take a long time. I actually feel really good about the productivity of the dev team this year, but we did not hit the goals that I set last year.

RICK (01:25:34.572)
You're executing a strategy. It's taking time for lots of reasons. There's no reason to change the strategy right now. You got to let it play. One question that I think you have some insecurity about rightfully is like in this age of AI in this age of new tooling, is there a way we could go faster than we are going? Yeah.

Tyler King (01:25:52.512)
Yeah, and I'm going to talk about that in a little bit. Yeah. Okay. My final goal last year was reduce the set of things I'm responsible for so I can focus on things I'm best at. that's what you kind of just, that's what I was just complimenting you on setting as your goal. Did I do that? Yeah, I think so. Not in like super tangible ways, but I do think maybe having a baby forces just cause I was like spending less time. There's no question if you came and looked over my shoulder for a month and looked at all the stuff I worked on, you'd

be able to point out things that seem like fat to you. I have a couple of recurring meetings that I probably don't have to have, et cetera. I have examined all of those and said basically, the other people in these meetings really value them. And I'm spending some of my time to keep them feeling like I'm bought into what they're working on. And it's not performative. I'm putting in FaceTime to show what I prioritize and I prioritize what they're working on, even though my contributions I don't think are that meaningful.

But I have been deliberate about, I've, I've cut a number of those types of things and I've kept some. I think Rob Michael, the head of the CRM coaching team has for many years run the team with very little involvement for me. Robert this year. I mean, it's been a gradual process over the years, but I think he's really more like Mike, like the team runs more like how CRM coaching does. I'm more involved in the sense that my individual contributor work is on the product side. So of course I'm more involved on the dev team.

But I'm not like, the dev team runs just fine without me. So I think I'm gonna mostly give myself, I'm gonna give myself a B on that

Um, so those are my goals. think I did. Okay. Um, the other updates from last year. So I built forms. We, we, didn't build it. We built it. Uh, the form builder talked about it a lot on this podcast, just to give an update on how it went. Um, the goal was by this time of year to get 4,000 submissions per week. Uh, just doing some rough guesses at the numbers. I thought that's what it would take to maybe have like a viral loop that mattered our actual.

Tyler King (01:28:00.128)
Right where we're at right now is we're getting about a thousand. So about 25 % of that goal. The trajectory was like the first half of the year we hit the, we were following the goal perfectly, but then we kind of saturated our current customer base and it didn't plateau. It is still growing. We're on pace for five years from now to hit that goal. So at this point, it's just kind of like set it and forget it. This was not a game changer. It wasn't a total failure though. We've got nine paying users from that we can track through those form clicks. That's nothing.

of course, presumably though, if we get nine people that actually clicked the powered by link and then signed up and then paid, presumably there's more benefit than just that. So I'm calling that like definitely not enough of a success that we should keep working on it or build another viral loop, but also not a total failure.

RICK (01:28:47.854)
I

Tyler King (01:28:50.342)
Um, summary on growth. already said, well, I said both of these were still plateaued. And the main metric I'm looking at right now is that trial to paid number. Uh, it did go, so it was at 32%. It went to 27 over this last year, almost exactly when we shipped forms and email logging, it went up to 28 from 27. Probably that's a mirage. Anytime you look at numbers, you know, there's just a little wiggling up and down. Probably this last year we got unlucky and this year we got lucky, but if

the CarPlay strategy is successful. If five years from now we look back and we're like, the CarPlay strategy worked, it's possible we have already seen the very, very beginning of it working. It's also very possible that that's nonsense that time will tell basically. Any thoughts on that before I move on?

RICK (01:29:37.986)
Nope. I wrote down that I admire your focus on a one metric that matters to drive your decision making. And I wrote down, you know, what, could that be for like up in 2026? I think it creates a lot of good focus.

Tyler King (01:29:52.002)
Yeah, that's interesting. So speaking of which segues perfectly in the next point, one thing I'm going to pat myself on the back for this year, I stayed focused. We as a company stayed focused on things that matter. This is the first year ever, I think, that the plan I had a year ago is the same as the plan I have now. We're actually going to change it next year, not because this plan is bad, but because we're going to have finished it and it will be time for the next thing.

Tyler King (01:30:22.398)
I keep a Kanban board in notion of the big projects we work on across the whole company each quarter. And I have them broken down into three columns or four columns. But the three main ones are, this is going to help with growth. Actually, there's two different growth related ones. And then there's kind of like a distraction column. Maybe we needed to do it, but it's not like we'd have to upgrade from PHP whatever to PHP whatever.

or upgrade to the new version of React. That's not helping with growth. In the years past, there's been a bunch of stuff in that distraction column. Last year, there was almost nothing. So I feel really good about that. And then the final updates from last year, the user forum, which I've talked about here. Still a lot of work to do there, but we have launched a user forum. I think that's one of the bigger marketing new ideas. Kind of a risk, right? That actually is a good example of taking the risk.

We avoided it for so long because it's like, what if it gets spammed? What if someone posts political stuff on there? What if one of our really great customers starts hounding us about a feature we don't want to build? There are all these reasons we didn't want to have a user forum. We decided whatever the upside outweighs the downside, we shipped it. So far, it's going OK. And then the final one is we started doing user interviews. Eunice, our head of marketing, but she's really kind of product marketing. I don't know what the right term is.

She's the right person to do user interviews. The only other person would be me. But again, in the spirit of like trying to protect my time, I think she's doing a great job of it. We're getting a lot of really good insights from these user interviews and I'm realizing we should have done this years ago and we should just keep doing it forever. And she's on board with that. She's just gonna keep interviewing users. And then I meet with her every other week. She synthesizes everything, gives it to me. I'm feeling really good about that cycle.

RICK (01:32:15.502)
This operationalizing user interviews, is this a no brainer? It's how I got our first 50 clients at Legapalph is user interviews. And it's just something, I think it's just like, how do you scale it is the question and make it intentional.

Tyler King (01:32:30.39)
Well, especially so the reason I didn't do that. It might sound like duh, of course you're supposed to do this. That wasn't lost on me before, but it's like, yeah, we have a team of eight CRM coaches that talk to users all the time. So one of the questions we're asking now is like, what's the difference between what Eunice is doing and what they're doing? Because interestingly, not only is she getting insights that I can take to make product decisions with, and that she can take to make marketing decisions with, I think she's converting more of those people into customers than our CRM coaches are with their customer service calls.

And that's not the point. Like she emails people after they have failed to pay and she's like, listen, I am not going to try to sell you. That's not the point of this. And she's, she means that she's not trying to sell them, but just something about how the calls are going. The customer on the other end is like, well, you know, huh, this has actually been a really great call. I'm to go give you guys another shot. so it's, it's almost working as a sales channel as well. So we, we are, I don't have an answer to that, but

I thought we were talking to customers and we were. We talked to thousands of customers a month on the phone. Is that right? Hundreds? Whatever. A lot. There's something different about a customer interview. Can we go backwards and say, okay, CRM coaches, you need to now be talking to customers the way Eunice is right now. So we'll see.

RICK (01:33:46.671)
That is very interesting. Or just give them a quote of one of those a month, where it's like you're proactively reaching out to someone to do an interview versus reacting to a support request.

Tyler King (01:33:48.994)
I wrote down.

Yeah.

Tyler King (01:33:59.618)
Yeah, absolutely. I've got a topic we'll talk about in different episode about that. Yeah. I've got some specific insights here, but I'll save that for like what we've learned from the interviews. I'll save that for when we talk about it deeper later too. So, okay. That was 2025. I feel pretty good about the professional side. Again, no output to show really, but the product's way better. I just, feel really good about where Less Knowing Serums are.

RICK (01:34:02.582)
I'd love to talk about that more. Let's definitely talk about that more.

RICK (01:34:26.146)
You should, mean, honestly, this year was incredible for you. You had a baby and, did a lot of stuff personally that to, to adapt to that. And then your, your business is highly focused and it's executed. Like, you don't know if the strategy is right or wrong, but you're executing it. Let's wait, what else can you ask for?

Tyler King (01:34:43.934)
Mm-hmm. Yeah, exactly.

And in the past, that hasn't been the case. In the past, it's been like, well, in January, we said we were going to do this, but then this came up and that came up and that came up. yeah. Okay. Thank you for saying that. 2026, professional goals. So for my individual contributor work, I just want to, I want to be even more focused. I want to spend almost all my time on design, product management and coding. What's not said in that goal is I don't want to be a CEO.

RICK (01:34:52.206)
Yeah.

Tyler King (01:35:20.124)
not like I want to stop being the CEO and hire a different one, but like, don't think this company needs 40 hours a week of CEO time. I think it needs one or two hours a week of CEO time. so one example of like something I cut last, I didn't cut, but I reduced last year. I used to send a company newsletter every single Sunday. It's really great. Absolutely. The CEO of a company should have a communication channel to send out messages to the whole team.

and they should be required to read it. But I didn't need it every week. And sometimes I'd find myself sitting there. I always wrote it on Sunday morning and I'd be sitting there on my computer like, huh, what am going to talk about this week? So I just switched the cadence to like, if I have something to say, I'll send it to you guys. And if I don't, I won't. Pretty straightforward, pretty simple. But now I'm spending half as much time doing that.

RICK (01:36:10.219)
And it's probably higher signal.

Tyler King (01:36:11.818)
Yes. Yeah. And something I don't think I appreciate it. Someone, one of my employees told me this in one of our one-on-ones. They were like, you know, it takes us time to read that, right? It's not just taking you time to write it.

RICK (01:36:22.766)
It's the easiest thing to forget as a leader is like, calculate the cost of something in terms of like the time it takes for you to produce it. But there is a domino impact across the org of anything you put out there. And it's a.

Tyler King (01:36:36.386)
Yeah, and there's 18 people reading it. So even if they read it much, much faster than it takes me to write it, it's 18. Mm-hmm, yeah.

RICK (01:36:41.014)
And then they're talking about it. And then they're probably interpreting something you're saying as a, ask of them and making, they're actioning it.

Tyler King (01:36:48.065)
Yeah.

Tyler King (01:36:51.584)
Yeah, so that's a good example of like that writing that newsletter. I'm still going to keep doing it, but that CEO work. My goal is to spend as much time as I can on design product management and coding. So like I'll write the newsletter when it's useful, but I'm not going to like. In the past, I've just made up excuses to do other stuff and I'm going to try to avoid that. There is some management stuff and all that though. My main management goal and this is what we've been hinting at this whole time.

I think I personally have been relatively speaking on the early side of AI adoption. If you recall two and a half years ago when I built the first leg up health app, was using like chat GPT. And I said this on the podcast, like it wouldn't gotten built without chat GPT. Like I was using it very heavily. I have chat GPT, Claude and cursor subscriptions. The thing is I don't code much. So the

problem is that the people actually writing the code for the company aren't doing this. I was hoping someone would step up. Like one of the developers would just say, we have a professional development system where someone could have said, hey, I want to take two weeks off my normal work, install Cloud Code, watch some YouTube videos, figure out how to get Cloud Code working really well. No one has done that.

A, there's kind of like a cultural question I need to ask about that, like... Are you clipping your nails?

RICK (01:38:19.95)
Yeah, sorry. had to real quick. I had a hangnail. Did you ever like hit a hangnail and you're like, okay, I could pull that off or I could clip it and I should clip it, but I'm, I was about to pull it off and like create a bad situation. And so then I was like, okay, I know I'm going to do this right now.

Tyler King (01:38:22.722)
you

Tyler King (01:38:26.178)
you

Tyler King (01:38:34.498)
Mm-hmm. So you've just got nail clippers at your desk all the time, 24-7. Wow. What is that?

RICK (01:38:39.532)
Yep, they're disguised in this. It's a nail clipper holder disguised as a. Sorry about that.

Tyler King (01:38:43.806)
Weird, he's showing what looks like a coin purse. Okay. So anyway, I, A, like I want the team. No, not at all. I want the team to feel more. I don't know. I'm a little, I wish someone had taken it upon themselves to do this. And I'm asking myself like, how do I create more of that culture? I think we have a culture right now of like, the leaders will tell me when I need to do something.

RICK (01:38:52.706)
Was that distracting to you, Tyler?

Tyler King (01:39:14.726)
which is good most of the time, sometimes it's like, no, you go do it, show some initiative here. So that's one part of it. But then also like no one has shown the initiative. So I need to do something to get the team using AI more. I don't know what.

RICK (01:39:29.006)
So there's two issues here I think you're saying. One is you wanna make sure you're not missing the AI train. And then the second thing is like evaluating why you're the one driving this versus someone else.

Tyler King (01:39:40.724)
Yeah. I, specifically one of the individual, I'm not saying like Robert, the manager, like he's, he's pushing a million new things all the time, but like, I'm surprised none of the individuals did it. And I'm not, I hope I'm, I'm not like putting them on blast publicly on the podcast. You're like, this, this is what I'm saying is the culture of the company is that they don't view that as their job, right? Not so it's, it's more a criticism of the culture I've created than them individually, I think.

RICK (01:40:10.914)
Have you said, like in your newsletter,

RICK (01:40:16.554)
Hey, this AI thing's coming. We're behind. Okay.

Tyler King (01:40:20.002)
Yes. I gave a whole, one of our six month presentations like a year and a half ago, yeah, a little over a year ago, fall of 2024. was like, AI is a big deal. It's coming. We need to use these tools. Like it was kind of vague because like this was before a lot of the recent stuff has happened, but I was like, we need to be on top of this. Like, like we've got a company of people that hate AI, including me, but it's like, you can hate it, but you still got to use it. So I gave that. then in every dev team meeting, we meet once a month.

and I have a permanent topic for the meeting every single time. I'm like, we're talking about AI. What are the new update? And when I said, hey, what do we think about MCP servers? No one knew what I was talking about. When I was like, hey, cloud code, like we've been using cursor, but like there's these terminal tools. No one knew what I was talking about. So just no one's following it at all. And I need to change that somehow. So I don't have specifics on how to do that, but I'm going to be thinking more about that.

RICK (01:41:17.23)
That's great. I would, yeah, I think it's great.

Tyler King (01:41:20.934)
next up is a project management goal, even without AI, but this is going to be really exacerbated. If I succeed at the AI thing, I just said, this is really going to be exacerbated. even without it, the dev team is more productive than ever before. And, I'm the only, so there's me and we have a contract, a design contractor. So me and a designer, we are struggling to keep up with the productivity of the devs right now.

just like making the cards. Again, we have a culture where it's not like I give them a project and they shape it. I shape every project. It's hard to keep up. And I feel like I've been letting some things slip through the cracks. So I need to figure out how to keep up. This could mean putting more of the responsibility on the devs. It could mean making myself more efficient. There may be, like I actually recently have started using AI to help me with design and

specing projects, which has been helping. So one way or another, I just need to be able to keep up with the devs.

RICK (01:42:27.138)
Yeah, it seems like AI is the answer here. Is like a first, like, is it?

Tyler King (01:42:31.072)
Yeah, but AI tools are way better for coding than they are for design and product management right now, I think. Figma AI sucks. It's terrible. Yeah. Well, and that's not the type of design I'm talking about though. Like Figma design is like, make me a homepage that looks okay. It's not like I need to figure out what the UX for this feature is going to be. Figma literally can't do that. Like their prompting system is like, we will one shot you.

RICK (01:42:36.97)
Even Figma? Do you use Figma? Really? I hear so many things about it.

Tyler King (01:42:58.602)
a design, as far as I can tell, they do not make any edits. And it's not about UX at all. It's entirely about the aesthetics of the design, which we already have a design system. Like when we're designing a new thing, it's like, I know what the button looks like. I know what the container, I know the typography, all of that's already set. It's just a question. No, well, I don't think so. I haven't seen any feature that does that. What has been really helpful. No, well, think about coding is all text. Like the output of the work.

RICK (01:43:13.207)
It won't do that for you?

RICK (01:43:21.092)
It seems like that'd be easier than coding.

Tyler King (01:43:27.986)
is in text, which is what LLMs work with. Like, there's no better use case for LLMs than coding, I don't think. Not that it can't be used for it, but the data to train on is all there. The design data, you only see these pixels as the artifact of what comes out.

RICK (01:43:44.856)
But Figma has that translated to actual code, right? So every design tracks back to some data version of, okay.

Tyler King (01:43:52.896)
Yeah, but that's not the hard part. That's not what we need help with. The hard part is like, okay, we need like all those things I was just talking about with Kanban, right? But like, okay, how do we think through this? How do like, when should the loading bar appear? Like how many cards should we show? Should we load with the initial state before it's just a lot of nuance that Figma is not getting close to touching that nuance.

RICK (01:44:17.367)
Yeah, and that's like, there's one thing of like, what's the experience for the user, the other is like, what's the logic? And that sounds like the, yeah, okay, got it.

Tyler King (01:44:24.256)
Yeah, both of those it's bad at, I think.

But what has been useful recently, chat GPT is good enough at image recognition now that I'll make a design in Figma, export it as an image, upload it to chat GPT and be like, okay, I've got this design. I think it's 80 % good, but there's these two trade-offs I can't figure out. Can you help me think through it? And it has never given me the right answer. It has never given me an answer I've used, but it has been a tremendously helpful.

Like in the past I would get blocked and I'd be like, I need to talk about this with Bracken or someone else on the team. And now I'm just like, I'm going to rubber duck this with chat GPT. It has unblocked me on design quite a

Have you done that? you uploaded an image to ChachiBT before? It's magic. You can give it a UI that you've designed and be like, what do you think about the copy? where things like it just, understands the whole thing. It's like, oh, I see on the right side, you've got this help section and like, it just knows what's going on and you can have a whole conversation about it without having to tell it anything.

RICK (01:45:27.938)
For my personal website project, do you think that I could use ChachiBT to basically design my personal website in Webflow? And like, tell me exactly what to do?

Tyler King (01:45:37.558)
I don't know about the things Webflow, like it wants to give you code and you can't with Webflow, you have to do it through the UI, right? I think you do. I don't think Webflow is the tool to use anymore for you. It's a tool to use for me or for a company because the idea is like the marketers have to be able to edit stuff and you have one person writing content and a different person doing design. like AI wants to output text and

RICK (01:45:46.434)
I don't know.

RICK (01:45:50.84)
Really.

Tyler King (01:46:05.73)
Text isn't what Webflow takes in as an input.

RICK (01:46:08.632)
So you would build a custom website.

Tyler King (01:46:11.264)
I or I haven't looked into the options, but it would be very, very easy. If you say to chat GPT, give me like just build or probably what you'd want to use is like Claude code or a Codex or one of these, like one of those types of tools. Or I think there there's actually more specific tools. Justin Jackson talks about one of them that he uses all the time. There are tools for this, but they don't turn into a web flow site. They turn into something else.

Vercell, think maybe has Vercell. It's, they have a product that's like build a website with AI or something. Well, you'd also want to, yeah.

RICK (01:46:50.926)
Okay, I'm gonna take, I thought this was like predetermined for me, Webflow, but I'm taking out that like maybe I need to like think about this more from an AI first perspective than like what I've been constrained before.

Tyler King (01:47:02.326)
You're definitely going to learn less about AI if you use Webflow.

RICK (01:47:05.592)
helpful. Thank you.

Tyler King (01:47:06.69)
Okay, wrapping up here, because we just got a few more minutes. So what I shared so far, spend more of my time on the product management coding and design stuff, get the team up to speed on AI, and figure out how to keep up with the devs. Those are more kind of like general, like you said, okay, our style goals, I think. Then the more concrete, like what do we want to ship on the product side?

Ship mobile and Kanban, of course, similar to how ship forms and email logging was the goal last year.

We've got a big theme, but there's one thing we're going to work on that's outside of that theme. And that is to reduce the amount of support we do by making things more self-serve. basically trying to identify, like we've talked about this before, if a serum coach leaves, I want to be able to not replace them. Even if they don't leave, I want the serum coaches to be able to spend more time on high impact stuff and less time just answering rogue questions. Exactly. Yes. So I almost got into that whole thing when we were talking about that, but we're going to, there are some product things we can do.

RICK (01:48:02.22)
Like customer interviews. Yeah.

Tyler King (01:48:11.308)
to reduce common customer service questions. Like an example of this is, if you've got a multi-user account, one of the users is the owner of the account. If they want to transfer ownership to a different user, they have to go through our support. We did this because it felt like accounts could get hijacked or whatever. That could be self-serve for sure. So we just have to build that into the product. 20 little things like that basically. Aside from that, everything is going to be in one single big theme. And that is, I think I...

I mentioned this to you before, the first 30 minutes. That's the theme of 2026 for us, the first 30 minutes, meaning anything that a person does not experience during the first 30 minutes of their free trial with LessonWing CRM, we're not working on. I've broken that into three subcategories. Onboarding, which is actually the smallest of these that might not, that might seem counterintuitive, but just like when you sign up, for example, picking smarter defaults.

allowing you to set up things without having to go into the settings page, enabling things by default rather than having you go in and just all that kind of stuff. Yeah, anything to say there? Just obvious.

RICK (01:49:21.386)
Increase time to I'm just like I'm just increased time trial to pay conversion. This is all that's all I'm thinking about right now.

Tyler King (01:49:25.954)
Absolutely. That's the broader one. Onboarding is one way to do that. Importing is the second big category. I think we could put the whole team on importing all year and not run out of things to do. One of the insights that's come out of customer interviews, because we had this big question. Stop me if I've already said this on the podcast, but we have upgraders and downgraders. Upgraders have a spreadsheet and they want something a little better.

Downgraders have a different CRM and they want something a little simpler.

RICK (01:49:56.44)
We have not talked about this, but this is brilliant. Okay, I love this.

Tyler King (01:50:00.202)
So here's going into the.

RICK (01:50:01.91)
I'm curious where do the downgraders come from?

Tyler King (01:50:05.038)
they just, they're running a business. Someone told them they need a CRM, Excel, sorry. Every single one of them is on Excel. Yeah, here's the thing. Every single one of them is on Excel. That's the insight. No, no, no, I know. So, okay. I thought upgraders were coming from Excel and downgraders were coming from Salesforce, HubSpot, PipeDrive. No, they're all coming from Excel. That's the big insight because the downgrader is paying for a CRM.

RICK (01:50:07.084)
What tool are they on?

The downgraders.

RICK (01:50:15.756)
I thought that's an upgrade.

RICK (01:50:23.086)
Yeah, yeah, that's what I thought.

What is the difference between downgrade versus upgrade?

Tyler King (01:50:30.572)
But the reason they're downgrading is because they never used it successfully. So all the data in it is garbage. None of them are actually importing data from their current CRM. Yeah, that's the big insight we got. You just had to listen to two hours and you got there.

RICK (01:50:38.958)
because they've given up on it. my God. Okay. So you're basically you're someone, your ICP is someone who has tried either is on a spreadsheet and is going to the CR for the first time or is on a spreadsheet but can't get off of it. And they've tried to get off of it before.

Tyler King (01:50:59.006)
Yep, yep. So this got way, I thought we had these two totally different types of customer to serve. We have one type of customer to serve. And the insight of even the people who already have CRMs and they're paying hundreds of dollars a month, whereas we're $15 a month. They're paying all this money for it and not using it. What happened is they imported their data, but it wasn't quite finished, right? They did that first session. They imported the data, but it didn't get finished.

And so the next time, you know, then they have to leave, they go to a meeting or whatever. The phone rings. It's a customer. It's a lead. They have to update something. Do they pull up their half finished HubSpot or do they pull up the spreadsheet? They pull up the spreadsheet.

RICK (01:51:38.306)
This was, this is so just to, this is JD. The reason like all we did in person together this year was get the CRM configured so that he would use it. Because if it wasn't configured in a way that was useful to him, it was just like, it was easier for him to just write it on a notepad or spreadsheet or that sort of thing.

Tyler King (01:51:48.449)
Mm-hmm.

Tyler King (01:51:55.702)
Yeah. So that's when I say the first 30 minutes, the reason this is so important, it's not just generic, of course onboarding is important. It's if the moment they leave, if the first session with the CRM, they don't get it fully set up, the next time the phone rings, they're not opening the CRM, they're opening their Excel sheet. And as soon as they enter anything in that spreadsheet, now all the data in the CRM is out of date and they're never going to come back. So we have to get them fully, fully onboarded in 30 minutes. That's the challenge for this year.

RICK (01:52:24.206)
And are you like, do you have in the product? Are you calling that out as a key part of onboarding? Like we know you, like we know. Yeah. I mean, that's cool. That's really cool. I mean, like talk about like a customer who under like feels like they're understood. if you can identify that and message around that, it's like, man.

Tyler King (01:52:32.266)
Not yet, but we're working on that, yeah.

Mm-hmm.

Tyler King (01:52:43.904)
Yeah, I'm just super excited about this. I think it's gonna help the product, it's gonna help the marketing, the positioning, all that. So importing's a huge part of that. They're all coming from a spreadsheet. Of course, every spreadsheet's different, but I think we can do a lot more, both to simplify it and to... Like right now, a lot of people import the spreadsheet and it's not the right format. And so then they have to talk to support and we're like, well, here's what you have to change about it. If we could just support 90 % of those different messy file formats.

Sorry, they're all the same file format, but the structure of the spreadsheet. Yeah, think, again, we just need to go from 28 % to 32 % trial conversion rate. And then the final category of this first 30 minutes thing is simplification. That's vague and doesn't mean much, but I talked about this before. identifying all the areas of our product that confuses people, and most of these are related to the data model.

the fact that contacts have leads attached to them and the lead has the status rather than just the contact having a status. The fact that your B2C, every time you add a contact and you enter a company name, it creates a company and that company shows up in your CRM. You don't want that company there. I've got a long list of those, but there's four in particular. I just said two of them. One of them, this is going to sound minor, but right now if you click on a contact in the CRM, it opens up a whole new page with their contact record.

With this first in this customer interviews, like what do our customers do with the CRM? They don't look at reports. They don't do analysis. They don't do forecasting. None of them. They work through their list. That's what they're doing. And our UI is not optimized for working through a list right now. You click on a contact. It takes you to the contact page. And then you have to click the back button and go back to the list and you lost your place in the list. So we're going to start opening. Yeah, yeah, I know. I've loved JD always pulls up pipe drive in our partner meetings and I'm like sitting there taking notes.

RICK (01:54:32.952)
Pipe Drive does this very well.

Yeah.

Tyler King (01:54:42.122)
So just doing that, like opening it as a dialogue on the page. And then when you, can just go back to your list. And then the final thing, this is gonna sound super basic, but just like a table view of context. Right now we have a very simple like address book view. It's like name, email, title, whatever. Just letting people, if they're used to using a spreadsheet, they upload their spreadsheet. And then the first thing they see is their spreadsheet, right?

RICK (01:55:05.122)
That's brilliant. Just like worst case, pay to use it in your shift your spreadsheet to less knowing CRM. That's brilliant. That should be number one, man.

Tyler King (01:55:12.47)
Yeah, exactly. And it's like a spreadsheet with tasks, a spreadsheet with.

It might be the first one we work on.

RICK (01:55:19.562)
Yeah, that one's brilliant. Like, hey, the first step in getting started with less annoying CRM is to start using less annoying CRM as your spreadsheet.

Tyler King (01:55:27.446)
Yeah, don't change anything about your workflow. get it. Now, the hard part about that is then we have to explain, well, why is this better than your spreadsheet? And there's a lot of reasons, but it muddies that message a little bit. So those are the four main things I would like to get in a perfect world. Some onboarding stuff, a brand new importing flow, and those four simplification projects shipped in 2026.

RICK (01:55:35.82)
Yeah. Yep.

RICK (01:55:50.158)
Woof. Wow. We did it.

Tyler King (01:55:53.9)
We'll see. We did it, two hours. We took all the time.

RICK (01:55:59.63)
What is it? Time fills the space, given it?

Tyler King (01:56:02.986)
Yeah, if we booked three hours, would this have taken three hours? No. All right.

RICK (01:56:07.084)
Probably not.

Anything, any final words on 2025?

Tyler King (01:56:14.818)
No, as always, appreciate having you as a, continuing to do this podcast. We're very close to 200 episodes. I think this is 195 or something. I thought your reflection and your updates, especially on the personal side were some good stuff this year. I'm glad you did that personally, but I'm also glad you shared it. think I've got a lot to think about now too.

RICK (01:56:37.172)
thank you Tyler for everything you do. mostly modeling. just, the, co-parenting, the thing I wrote down that I'm taking away and I'm go talk to you all about is co-parenting is great. Still, the parenting is hard and I want to do more co-parenting in 2025, 2026.

Tyler King (01:56:48.768)
Yeah. More co-parenting next year. Listeners, more co-parenting.

RICK (01:56:55.595)
And Tyler's got a big decision to make. All right. If you'd to review past topics and show notes, visit star of the last.com. See you next week.

Tyler King (01:56:59.074)
My parents listen to this,

Tyler King (01:57:08.246)
See ya.